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Volumn 9, Issue 3, 2012, Pages 310-341

Stereoselective synthesis of α-aminophosphonic acids analogs of the 20 proteinogenic α-amino acids

Author keywords

Biological activity; Resolution; Stereoselective synthesis; amino acids; aminophosphonates; Aminophosphonic acids

Indexed keywords


EID: 84861163776     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017912801270595     Document Type: Review
Times cited : (57)

References (246)
  • 1
    • 67650230587 scopus 로고    scopus 로고
    • Irreversible inhibition of serine proteasesdesign and in vivo activity of diaryl α-aminophosphonate derivatives
    • Sieαczyk, M.; Oleksyszyn, J. Irreversible inhibition of serine proteasesdesign and in vivo activity of diaryl α-aminophosphonate derivatives. Curr. Med. Chem. 2009, 16, 1673-1687.
    • (2009) Curr. Med. Chem. , vol.16 , pp. 1673-1687
    • Sieαczyk, M.1    Oleksyszyn, J.2
  • 2
    • 0003563365 scopus 로고    scopus 로고
    • Aminophosphonic and Aminophosphinic Acids., Kukhar, VP.; Hudson, H, R., Eds.; John Wiley & Sons: Chichester, UK
    • Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; John Wiley & Sons: Chichester, UK, 2000.
    • (2000) Chemistry and Biological Activity
  • 3
    • 84913150907 scopus 로고
    • Biological activity of aminophosphonic acids. βPhosphorus, Sulfur Silicon Relat
    • Kafarski, P.; Lejczak, B. Biological activity of aminophosphonic acids. βPhosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193-215.
    • (1991) Elem. , vol.63 , pp. 193-215
    • Kafarski, P.1    Lejczak, B.2
  • 4
    • 0000899405 scopus 로고
    • Optically active 1-aminoalkylphosphonic acids
    • Dhawan, B.; Redmore, D. Optically active 1-aminoalkylphosphonic acids. Phosphorus Sulfur 1987, 32, 119-144.
    • (1987) Phosphorus Sulfur , vol.32 , pp. 119-144
    • Dhawan, B.1    Redmore, D.2
  • 5
    • 0347625851 scopus 로고    scopus 로고
    • Contribution of molecular modeling and site-directed mutagenesis to the identification of a new residue, glutamate 215, involve in the exopeptidase specificity of aminopeptidase A
    • Rozenfeld, R.; Iturrioz, X.; Okada, M.; Maigret, B.; Llorents-Cortes, C. Contribution of molecular modeling and site-directed mutagenesis to the identification of a new residue, glutamate 215, involve in the exopeptidase specificity of aminopeptidase A. Biochemistry 2003, 42, 14785-14793.
    • (2003) Biochemistry , vol.42 , pp. 14785-14793
    • Rozenfeld, R.1    Iturrioz, X.2    Okada, M.3    Maigret, B.4    Llorents-Cortes, C.5
  • 6
    • 0030818538 scopus 로고    scopus 로고
    • Phosphonate diester and phosphonamide synthesis Reaction coordinate analysis by 31P NMR spectroscopy: Identification of pyrophosphonate anhydrides and highly reactive phosphonylammonium salts
    • Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, III, A. B. Phosphonate diester and phosphonamide synthesis. Reaction coordinate analysis by 31P NMR spectroscopy: identification of pyrophosphonate anhydrides and highly reactive phosphonylammonium salts. J. Am. Chem. Soc. 1997, 119, 8177-8190.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8177-8190
    • Hirschmann, R.1    Yager, K.M.2    Taylor, C.M.3    Witherington, J.4    Sprengler, P.A.5    Phillips, B.W.6    Moore, W.7    Smith III, A.B.8
  • 8
    • 0025979246 scopus 로고
    • Irreversible inhibition of serine proteases by peptide derivatives of (α-aminoalkyl)phosphonate diphenyl esters
    • Oleksyszyn, J.; Powers, J. C. Irreversible inhibition of serine proteases by peptide derivatives of (α-aminoalkyl)phosphonate diphenyl esters. Biochemistry 1991, 30, 485-493.
    • (1991) Biochemistry , vol.30 , pp. 485-493
    • Oleksyszyn, J.1    Powers, J.C.2
  • 9
    • 0024409372 scopus 로고
    • Renin inhibitors Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond
    • Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J. Med. Chem. 1989, 32, 1652-1661.
    • (1989) J. Med. Chem. , vol.32 , pp. 1652-1661
    • Allen, M.C.1    Fuhrer, W.2    Tuck, B.3    Wade, R.4    Wood, J.M.5
  • 10
    • 0023277991 scopus 로고
    • Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase
    • Giannousis, P. P.; Bartlett, P. A. Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase. J. Med. Chem. 1987, 30, 1603-1609.
    • (1987) J. Med. Chem. , vol.30 , pp. 1603-1609
    • Giannousis, P.P.1    Bartlett, P.A.2
  • 11
    • 0141786949 scopus 로고    scopus 로고
    • Rapid parallel synthesis of dipeptide diphenyl phosphonate esters as inhibitors of dipeptidyl peptidases
    • For some examples on the synthesis of phosphono-peptides see
    • For some examples on the synthesis of phosphono-peptides see Senten, K.; Daniëls, L.; Van der Veken, P.; De Meester, I.; Lambeir, A.-M.; Scharpé, S.; Haemers, A.; Augustyns, K. Rapid parallel synthesis of dipeptide diphenyl phosphonate esters as inhibitors of dipeptidyl peptidases. J. Comb. Chem. 2003, 5, 336-344.
    • (2003) J. Comb. Chem. , vol.5 , pp. 336-344
    • Senten, K.1    Daniëls, L.2    van der Veken, P.3    de Meester, I.4    Lambeir, A.-M.5    Scharpé, S.6    Haemers, A.7    Augustyns, K.8
  • 12
    • 0035945011 scopus 로고    scopus 로고
    • Polymer-assisted solution-phase parallel synthesis of dipeptide p-nitroanilides and dipeptide diphenyl phosphonates
    • Senten, K.; Van der Veken, P.; Bal. G.; Hae mers, A.; Augustyns, K. Polymer-assisted solution-phase parallel synthesis of dipeptide p-nitroanilides and dipeptide diphenyl phosphonates. Tetrahedron Lett. 2001, 42, 9135-9138.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 9135-9138
    • Senten, K.1    van der Veken, P.2    Bal, G.3    Hae mers, A.4    Augustyns, K.5
  • 13
    • 0035906032 scopus 로고    scopus 로고
    • OEthyl 1-azidoalkylphosphonic acids-versatile reagents for the synthesis of protected phosphonamidate peptides
    • Sikora, D.; Nonas, T.; Gajda, T. OEthyl 1-azidoalkylphosphonic acids-versatile reagents for the synthesis of protected phosphonamidate peptides. Tetrahedron 2001, 57, 1619-1625.
    • (2001) Tetrahedron , vol.57 , pp. 1619-1625
    • Sikora, D.1    Nonas, T.2    Gajda, T.3
  • 14
    • 0028134093 scopus 로고
    • Solid-phase synthesis of peptidylphosphonates
    • Cambell, D. A.; Bermak, J. C. Solid-phase synthesis of peptidylphosphonates. J. Am. Chem. Soc. 1994, 116, 6039-6040.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6039-6040
    • Cambell, D.A.1    Bermak, J.C.2
  • 15
    • 33845278913 scopus 로고
    • Synthesis of phosphonic acid derivatives by oxidative activation of phosphinate esters
    • Sampson, N. S.; Batlett, P. A. Synthesis of phosphonic acid derivatives by oxidative activation of phosphinate esters. J. Org. Chem. 1988, 53, 4500-4503.
    • (1988) J. Org. Chem. , vol.53 , pp. 4500-4503
    • Sampson, N.S.1    Batlett, P.A.2
  • 19
    • 0034083373 scopus 로고    scopus 로고
    • Synthesis of N-alkyl-(α-aminoalkyl)phosphine oxides and phosphonic esters as potential HIVprotease inhibitors, starting from α-aminoacids
    • Alonso, E.; Solis, A.; del Pozo, C. Synthesis of N-alkyl-(α-aminoalkyl)phosphine oxides and phosphonic esters as potential HIVprotease inhibitors, starting from α-aminoacids. Synlett 2000, 698-700.
    • (2000) Synlett , pp. 698-700
    • Alonso, E.1    Solis, A.2    del Pozo, C.3
  • 21
    • 0026438772 scopus 로고
    • Synthesis of stereochemically defined phosphonamidate-containing peptides: Inhibitors for the HIV-1 proteinase
    • Camp, N. P.; Hawkins, P. C. D.; Hitchcock, P. B.; Gani, D. Synthesis of stereochemically defined phosphonamidate-containing peptides: inhibitors for the HIV-1 proteinase. Bioorg. Med. Chem. Lett. 1992, 2, 1047-1052.
    • (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 1047-1052
    • Camp, N.P.1    Hawkins, P.C.D.2    Hitchcock, P.B.3    Gani, D.4
  • 23
    • 0022577081 scopus 로고
    • Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
    • Atherton, F. R.; Hassall, C. H.; Lambert, R. W. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. J. Med. Chem. 1986, 29, 29-40.
    • (1986) J. Med. Chem. , vol.29 , pp. 29-40
    • Atherton, F.R.1    Hassall, C.H.2    Lambert, R.W.3
  • 24
    • 0023034922 scopus 로고
    • Antibacterial activity of phosphonodipeptides related to alafosfalin
    • Lejczak, B.; Kafarski, P.; Sztajer, H.; Mastalerz, P. Antibacterial activity of phosphonodipeptides related to alafosfalin. J. Med. Chem. 1986, 29, 2212-2217.
    • (1986) J. Med. Chem. , vol.29 , pp. 2212-2217
    • Lejczak, B.1    Kafarski, P.2    Sztajer, H.3    Mastalerz, P.4
  • 25
    • 31544482713 scopus 로고    scopus 로고
    • Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-γ-[ωP(O)(OH)]-glutarate, a potent inhibitor of folypoly-γ-glutamate synthetase: Synthesis and hydrolytic stability
    • Feng, Y.; Coward, J. K. Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-γ-[ωP(O)(OH)]-glutarate, a potent inhibitor of folypoly-γ-glutamate synthetase: synthesis and hydrolytic stability. J. Med. Chem. 2006, 49, 770-788.
    • (2006) J. Med. Chem. , vol.49 , pp. 770-788
    • Feng, Y.1    Coward, J.K.2
  • 26
    • 0001624368 scopus 로고    scopus 로고
    • Aminophosphonic acids of potential medical importance
    • Kafarski, P.; Lejczak, B. Aminophosphonic acids of potential medical importance. Curr. Med. Chem. 2001, 1, 301-312.
    • (2001) Curr. Med. Chem. , vol.1 , pp. 301-312
    • Kafarski, P.1    Lejczak, B.2
  • 27
  • 28
    • 0034499290 scopus 로고    scopus 로고
    • An overview of recent advances on the synthesis and biological activity of α-aminophosphonic acid derivatives
    • Huang, J.; Chen, R. An overview of recent advances on the synthesis and biological activity of α-aminophosphonic acid derivatives. Heteroatom. Chem. 2000, 11, 480-492.
    • (2000) Heteroatom. Chem. , vol.11 , pp. 480-492
    • Huang, J.1    Chen, R.2
  • 29
    • 82855179830 scopus 로고
    • Organic phosphorus compounds: Preparation, physical and biological properties of aminoarylmethylphosphonic and phosphonous acids
    • Maier, L.; Diel, P. J. Organic phosphorus compounds: preparation, physical and biological properties of aminoarylmethylphosphonic and phosphonous acids. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 57, 57-64.
    • (1991) Phosphorus, Sulfur Silicon Relat. Elem. , vol.57 , pp. 57-64
    • Maier, L.1    Diel, P.J.2
  • 30
    • 0001570391 scopus 로고
    • Binding ability of pesticides X-ray, spectroscopic, and polarographic studies of the copper (II) interaction with acifluorfen
    • Kozlowski, H.; Pusino, A.; Swiatek, J.; Spychala, J.; Glowiak, T.; Micera, G.; Gessa, C. Binding ability of pesticides. X-ray, spectroscopic, and polarographic studies of the copper (II) interaction with acifluorfen. J. Agric. Food Chem. 1990, 38, 1989-1992.
    • (1990) J. Agric. Food Chem. , vol.38 , pp. 1989-1992
    • Kozlowski, H.1    Pusino, A.2    Swiatek, J.3    Spychala, J.4    Glowiak, T.5    Micera, G.6    Gessa, C.7
  • 31
    • 0036420749 scopus 로고    scopus 로고
    • Antioxidative activity of some phenoxy and organophosphorous compounds
    • Nska, H.; Bonarska, D.; Bielecki, K.; Sarapuk, J. Antioxidative activity of some phenoxy and organophosphorous compounds. Cell. Mol. Biol. Lett. 2002, 7, 929-935.
    • (2002) Cell. Mol. Biol. Lett. , vol.7 , pp. 929-935
    • Nska, H.1    Bonarska, D.2    Bielecki, K.3    Sarapuk, J.4
  • 32
    • 0040931016 scopus 로고
    • Synthesis and properties of a novel aminophosphonic acid as an extracting agent for metals
    • Jagodic, V.; Herak, M. J. Synthesis and properties of a novel aminophosphonic acid as an extracting agent for metals. J. Inorg. Nucl. Chem. 1970, 32, 1323-1332.
    • (1970) J. Inorg. Nucl. Chem. , vol.32 , pp. 1323-1332
    • Jagodic, V.1    Herak, M.J.2
  • 33
    • 0141506639 scopus 로고
    • Transition metal complexes of dialkyl α-hydroxyiminophosphonates, a novel class of metal complexes
    • and references cited therein
    • Bligh, S. W. A.; Choi, N.; Green, D. St. C.; Hudson, H. R.; McGrath, C. M.; McPartlin, M.; Pianka, M. Transition metal complexes of dialkyl α-hydroxyiminophosphonates, a novel class of metal complexes. Polyhedron 1993, 12, 2887-2890 and references cited therein.
    • (1993) Polyhedron , vol.12 , pp. 2887-2890
    • Bligh, S.W.A.1    Choi, N.2    StGreen, D.C.3    Hudson, H.R.4    McGrath, C.M.5    McPartlin, M.6    Pianka, M.7
  • 34
    • 0001576843 scopus 로고
    • In, Priest, N. O.; Van de Vyver, F. L. Eds., CRC Press: Boca Raton, FL
    • Bulman, R. A. In Trace Metals and Fluoride in Bones and Teeth, Priest, N. O.; Van de Vyver, F. L. Eds., CRC Press: Boca Raton, FL, 1990; p. 271.
    • (1990) Trace Metals and Fluoride in Bones and Teeth , pp. 271
    • Bulman, R.A.1
  • 35
    • 1542690351 scopus 로고
    • Phosphonates as analogues of natural phosphates
    • Engel, R. Phosphonates as analogues of natural phosphates. Chem. Rev. 1977, 77, 349-367.
    • (1977) Chem. Rev. , vol.77 , pp. 349-367
    • Engel, R.1
  • 36
    • 56949101063 scopus 로고    scopus 로고
    • An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives
    • Ordóñez, M.; Rojas-Cabrera, H.; Cativiela, C. An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives. Tetrahedron 2009, 65, 17-49.
    • (2009) Tetrahedron , vol.65 , pp. 17-49
    • Ordóñez, M.1    Rojas-Cabrera, H.2    Cativiela, C.3
  • 37
    • 47749154512 scopus 로고    scopus 로고
    • Some potential chiral catalysts for preparation of asymmetric α-aminophosphonates
    • Bhadury, P. S.; Song, B.-A.; Yang, S.; Zhang, Y.; Zhang, S. Some potential chiral catalysts for preparation of asymmetric α-aminophosphonates. Curr. Org. Synth. 2008, 5, 134-150.
    • (2008) Curr. Org. Synth. , vol.5 , pp. 134-150
    • Bhadury, P.S.1    Song, B.-A.2    Yang, S.3    Zhang, Y.4    Zhang, S.5
  • 38
    • 49249117085 scopus 로고    scopus 로고
    • Catalytic enantioselective hydrophosphonylation of aldehydes and imines
    • Merino, P.; Marqués-López, E.; Herrera, R. P. Catalytic enantioselective hydrophosphonylation of aldehydes and imines. Adv. Synth. Catal. 2008, 350, 1195-1208.
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 1195-1208
    • Merino, P.1    Marqués-López, E.2    Herrera, R.P.3
  • 39
    • 33745390196 scopus 로고    scopus 로고
    • Catalytic asymmetric synthesis of α-and α-aminoalkanephosphonic acid derivatives
    • Ma, J.-A. Catalytic asymmetric synthesis of α-and α-aminoalkanephosphonic acid derivatives. Chem. Soc. Rev. 2006, 35, 630-636.
    • (2006) Chem. Soc. Rev. , vol.35 , pp. 630-636
    • Ma, J.-A.1
  • 40
    • 0008307835 scopus 로고    scopus 로고
    • Synthesis of racemic and optically active α-aminophosphonic acids
    • Uziel, J.; Genêt, J. P. Synthesis of racemic and optically active α-aminophosphonic acids. Russ. J. Org. Chem. 1997, 33, 1521-1542.
    • (1997) Russ. J. Org. Chem. , vol.33 , pp. 1521-1542
    • Uziel, J.1    Genêt, J.P.2
  • 42
    • 0042665702 scopus 로고    scopus 로고
    • Stereoselective synthesis of 1-aminoalkanephosphonic acids with two chiral centers and their activity towards leucine aminopeptidase
    • Drag, M.; Pawelczak, M.; Kafarski, P. Stereoselective synthesis of 1-aminoalkanephosphonic acids with two chiral centers and their activity towards leucine aminopeptidase. Chirality 2003, 15, S104-S107.
    • (2003) Chirality , vol.15
    • Drag, M.1    Pawelczak, M.2    Kafarski, P.3
  • 43
    • 0013610276 scopus 로고
    • 1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids
    • Baylis, E. K.; Campbell, C. D.; Dingwall, J. G. 1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids. J. Chem. Soc., Perkin Trans 1 1984, 2845-2853.
    • (1984) J. Chem. Soc., Perkin Trans 1 , pp. 2845-2853
    • Baylis, E.K.1    Campbell, C.D.2    Dingwall, J.G.3
  • 46
    • 0034792021 scopus 로고    scopus 로고
    • The membrane-disrupting activity of α-aminoalkanephosphonic acids and their derivatives
    • and references cited therein
    • Deron, A.; Dziamska, A.; Pawlaczyk, I.; Bielecki, K.; Kleszczyska, H.; Gancarz, R.; Sarapuk, J. The membrane-disrupting activity of α-aminoalkanephosphonic acids and their derivatives. Cell. Mol. Biol. Lett. 2001, 6, 291-297 and references cited therein.
    • (2001) Cell. Mol. Biol. Lett. , vol.6 , pp. 291-297
    • Deron, A.1    Dziamska, A.2    Pawlaczyk, I.3    Bielecki, K.4    Kleszczyska, H.5    Gancarz, R.6    Sarapuk, J.7
  • 47
    • 41849092226 scopus 로고    scopus 로고
    • Aminomethylphosphonic acid accumulation in plant species trated with glyphosate
    • Reddy, K. N.; Rimando, A. M.; Duke, S. O.; Nandula, V. K. Aminomethylphosphonic acid accumulation in plant species trated with glyphosate. J. Agric. Food Chem. 2008, 56, 2125-2130.
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 2125-2130
    • Reddy, K.N.1    Rimando, A.M.2    Duke, S.O.3    Nandula, V.K.4
  • 48
    • 0037226084 scopus 로고    scopus 로고
    • Isoflavone, glyphosate, and aminomethyl-phosphonic acid levels in seeds of glyphosate-treated, glyphosateresistant soybean
    • Duke, S. O.; Rimando, A. M.; Pace, P. F.; Reddy, K. N.; Smeda, R. J. Isoflavone, glyphosate, and aminomethyl-phosphonic acid levels in seeds of glyphosate-treated, glyphosateresistant soybean. J. Agric. Food Chem. 2003, 51, 340-344.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 340-344
    • Duke, S.O.1    Rimando, A.M.2    Pace, P.F.3    Reddy, K.N.4    Smeda, R.J.5
  • 49
    • 0037716457 scopus 로고    scopus 로고
    • Simultaneous analysis of biologically active aminoalkanephosphonic acids
    • and references cited therein
    • Kudzin, Z. H.; Gralak, D. K.; Adrijewski, G.; Drabowicz, J.; Uczak, J. Simultaneous analysis of biologically active aminoalkanephosphonic acids. J. Chromatogr. A 2003, 998, 183-199 and references cited therein.
    • (2003) J. Chromatogr. A , vol.998 , pp. 183-199
    • Kudzin, Z.H.1    Gralak, D.K.2    Adrijewski, G.3    Drabowicz, J.4    Uczak, J.5
  • 51
    • 0030818538 scopus 로고    scopus 로고
    • Phosphonate diester and phosphonamide synthesis Reaction coordinate analysis by 31P NMR spectroscopy: Identification of pyrophosphonate anhydrides and highly reactive phosphonylammonium salts
    • Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengler, P. A.; Phillips, B. W.; Moore, W.; Smith, III, A. B. Phosphonate diester and phosphonamide synthesis. Reaction coordinate analysis by 31P NMR spectroscopy: identification of pyrophosphonate anhydrides and highly reactive phosphonylammonium salts. J. Am. Chem. Soc. 1997, 119, 8177-8190.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8177-8190
    • Hirschmann, R.1    Yager, K.M.2    Taylor, C.M.3    Witherington, J.4    Sprengler, P.A.5    Phillips, B.W.6    Moore, W.7    Smith III, A.B.8
  • 52
    • 0001718823 scopus 로고
    • Peptides containing aminophosphonic acids 3. Synthesis of tripeptide containing aminomethylphosphonic acid
    • Yamauchi, K.; Mitsuda, Y.; Kinoshita, M. Peptides containing aminophosphonic acids 3. Synthesis of tripeptide containing aminomethylphosphonic acid. Bull. Chem. Soc. Jpn. 1975, 48, 3285-3286.
    • (1975) Bull. Chem. Soc. Jpn. , vol.48 , pp. 3285-3286
    • Yamauchi, K.1    Mitsuda, Y.2    Kinoshita, M.3
  • 53
    • 0000185336 scopus 로고
    • Peptides containing aminophosphonic acids II The synthesis of tripeptide analogs
    • Yamauchi, K.; Kinoshita, M.; Imoto, M. Peptides containing aminophosphonic acids II. The synthesis of tripeptide analogs. Bull. Chem. Soc. Jpn. 1972, 45, 2531-2534.
    • (1972) Bull. Chem. Soc. Jpn. , vol.45 , pp. 2531-2534
    • Yamauchi, K.1    Kinoshita, M.2    Imoto, M.3
  • 54
    • 0027976825 scopus 로고
    • Characterization of covalently bound enzyme inhibitors as transition-state analogs by protein stability measurements: Phosphonate monoester inhibitors of β-lactamase
    • Rahil, J.; Pratt, F. R. Characterization of covalently bound enzyme inhibitors as transition-state analogs by protein stability measurements: phosphonate monoester inhibitors of β-lactamase. Biochemistry 1994, 33, 116-125.
    • (1994) Biochemistry , vol.33 , pp. 116-125
    • Rahil, J.1    Pratt, F.R.2
  • 55
    • 0027495528 scopus 로고
    • Structure-activity relationships in the inhibition of serine β-lactamases by phosphonic acid derivatives
    • Rahil, J.; Pratt R. F. Structure-activity relationships in the inhibition of serine β-lactamases by phosphonic acid derivatives. Biochem. J. 1993, 296, 389-393.
    • (1993) Biochem. J. , vol.296 , pp. 389-393
    • Rahil, J.1    Pratt, R.F.2
  • 56
    • 0024370749 scopus 로고
    • Inhibition of a class C β-lactamase by a specific phosphonate monoester
    • Pratt, R. F. Inhibition of a class C β-lactamase by a specific phosphonate monoester. Science 1989, 246, 917-919.
    • (1989) Science , vol.246 , pp. 917-919
    • Pratt, R.F.1
  • 57
    • 0023667707 scopus 로고
    • Possible role for water dissociation in the slow binding of phosphorus-containing transition-state-analog inhibitors of thermolysin
    • Bartlett, P. A.; Marlowe, C. K. Possible role for water dissociation in the slow binding of phosphorus-containing transition-state-analog inhibitors of thermolysin. Biochemistry 1987, 26, 8553-8561.
    • (1987) Biochemistry , vol.26 , pp. 8553-8561
    • Bartlett, P.A.1    Marlowe, C.K.2
  • 58
    • 0029865582 scopus 로고    scopus 로고
    • Phosphonamidate analogues of dipeptides with carboxypeptidase A and β-lactamase-inhibitory activity: Elucidation of the mechanism of β-lactamase inhibition by electrospray mass spectrometry
    • Payne, D. J.; Bateson, J. H.; Tolson, D. A.; Gasson, B. C.; Khushi, T.; Ledent, P.; Fere, J. M. Phosphonamidate analogues of dipeptides with carboxypeptidase A and β-lactamase-inhibitory activity: elucidation of the mechanism of β-lactamase inhibition by electrospray mass spectrometry. Biochem. J. 1996, 314, 457-461.
    • (1996) Biochem. J. , vol.314 , pp. 457-461
    • Payne, D.J.1    Bateson, J.H.2    Tolson, D.A.3    Gasson, B.C.4    Khushi, T.5    Ledent, P.6    Fere, J.M.7
  • 60
    • 0030847769 scopus 로고    scopus 로고
    • Structure-activity studies of the inhibition of serine β-lactamases by phosphonate monoesters
    • Li, N.; Rahil, J.; Wright, M. E.; Pratt, R. F. Structure-activity studies of the inhibition of serine β-lactamases by phosphonate monoesters. Bioorg. Med. Chem. 1997, 5, 1783-1788.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 1783-1788
    • Li, N.1    Rahil, J.2    Wright, M.E.3    Pratt, R.F.4
  • 63
    • 0000176550 scopus 로고
    • Comments on the synthesis of aminomethylphosphonic acid
    • Soroka, M. Comments on the synthesis of aminomethylphosphonic acid. Synthesis 1989, 547-548.
    • (1989) Synthesis , pp. 547-548
    • Soroka, M.1
  • 64
    • 84953999914 scopus 로고
    • A convenient synthesis of aminomethylphosphonic acid
    • Pulwer, M. J.; Balthazor, T. M. A convenient synthesis of aminomethylphosphonic acid. Synth. Commun. 1986, 16, 733-739.
    • (1986) Synth. Commun. , vol.16 , pp. 733-739
    • Pulwer, M.J.1    Balthazor, T.M.2
  • 65
    • 84986418178 scopus 로고
    • Aminomethanephosphonic acid and its diphenyl ester
    • Oleksyszyn, J.; Subotkowska, L. Aminomethanephosphonic acid and its diphenyl ester. Synthesis 1980, 906-906.
    • (1980) Synthesis , pp. 906
    • Oleksyszyn, J.1    Subotkowska, L.2
  • 66
    • 0015750978 scopus 로고
    • Total synthesis of β-lactam antibiotics I α-thioformamido-diethylphosphonoacetates
    • Ratcliffe, R. W.; Christensen, B. G. Total synthesis of β-lactam antibiotics I. α-thioformamido-diethylphosphonoacetates. Tetrahedron Lett. 1973, 14, 4645-4648.
    • (1973) Tetrahedron Lett. , vol.14 , pp. 4645-4648
    • Ratcliffe, R.W.1    Christensen, B.G.2
  • 67
    • 0012835444 scopus 로고
    • Stabilization demands of diethyl phosphonate substituted carbocations as revealed by substituent effects
    • For the synthesis of diethyl phosphonomethyl-triflate, see
    • For the synthesis of diethyl phosphonomethyl-triflate, see: Creary, X.; Underiner, T. L. Stabilization demands of diethyl phosphonate substituted carbocations as revealed by substituent effects. J. Org. Chem. 1985, 50, 2165-2170.
    • (1985) J. Org. Chem. , vol.50 , pp. 2165-2170
    • Creary, X.1    Underiner, T.L.2
  • 68
    • 0000444481 scopus 로고
    • Synthesis and reactivity of diethyl phosphonomethyltriflate
    • Phillion, D. P.; Andrew, S. S. Synthesis and reactivity of diethyl phosphonomethyltriflate. Tetrahedron Lett. 1986, 27, 1477-1480.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1477-1480
    • Phillion, D.P.1    Andrew, S.S.2
  • 69
    • 84986674101 scopus 로고
    • Synthesis of 1-aminoalkylphosphonic acids via amidoalkylation of phosphorous acid by N, N'-alkylidenebisamides
    • Soroka, M.; Jaworska, D.; Szczsny, Z. Synthesis of 1-aminoalkylphosphonic acids via amidoalkylation of phosphorous acid by N, N'-alkylidenebisamides. Liebigs Ann. Chem. 1990, 1153-1155.
    • (1990) Liebigs Ann. Chem. , pp. 1153-1155
    • Soroka, M.1    Jaworska, D.2    Szczsny, Z.3
  • 70
    • 84986706380 scopus 로고
    • The synthesis of 1-aminoalkylphosphonic acids. A revised mechanism of the reaction of phosphorus trichloride, amides and aldehydes or ketones in acetic acid (Oleksyszyn reaction)
    • Soroka, M. The synthesis of 1-aminoalkylphosphonic acids. A revised mechanism of the reaction of phosphorus trichloride, amides and aldehydes or ketones in acetic acid (Oleksyszyn reaction). Liebigs Ann. Chem. 1990, 331-334.
    • (1990) Liebigs Ann. Chem. , pp. 331-334
    • Soroka, M.1
  • 71
    • 2442688922 scopus 로고    scopus 로고
    • Transport of the phosphonodipeptide alafosfalin by the H+/peptide cotransporters PEPT1 and PEPT2 in intestinal and renal epithelial cells
    • For the biological activity of (S, R)-alafosfalin, see
    • For the biological activity of (S, R)-alafosfalin, see: Neumann, J.; Bruch, M.; Gebauer, S.; Brandsch, M. Transport of the phosphonodipeptide alafosfalin by the H+/peptide cotransporters PEPT1 and PEPT2 in intestinal and renal epithelial cells. Eur. J. Biochem. 2004, 271, 2012-2017.
    • (2004) Eur. J. Biochem. , vol.271 , pp. 2012-2017
    • Neumann, J.1    Bruch, M.2    Gebauer, S.3    Brandsch, M.4
  • 73
    • 0019128997 scopus 로고
    • Phosphonopeptide antibacterial agents related to alafosfalin: Design, synthesis, and structure-activity relationships
    • Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Lloyd, W. J.; Ringrose, P. S. Phosphonopeptide antibacterial agents related to alafosfalin: design, synthesis, and structure-activity relationships. Antimicrob. Agents Chemother. 1980, 18, 897-905.
    • (1980) Antimicrob. Agents Chemother. , vol.18 , pp. 897-905
    • Atherton, F.R.1    Hall, M.J.2    Hassall, C.H.3    Lambert, R.W.4    Lloyd, W.J.5    Ringrose, P.S.6
  • 74
    • 53749093104 scopus 로고    scopus 로고
    • Preparation and transmetallation of enantioenriched α-aminoorganostannanes derived from N-Boc phenylglycinol: Application to the synthesis of alafosfalin
    • Coeffard, V.; Beaudet, I.; Evain, M.; Grognec, E. L.; Quintard, J.-P. Preparation and transmetallation of enantioenriched α-aminoorganostannanes derived from N-Boc phenylglycinol: application to the synthesis of alafosfalin. Eur. J. Org. Chem. 2008, 3344-3351.
    • (2008) Eur. J. Org. Chem. , pp. 3344-3351
    • Coeffard, V.1    Beaudet, I.2    Evain, M.3    Grognec, E.L.4    Quintard, J.-P.5
  • 75
    • 56249120996 scopus 로고    scopus 로고
    • Synthesis of alafosfalin and its phosphinic analogue and their fungicidal activity
    • Khomutov, R. M.; Osipova, T. I.; Khurs, E. N.; Dzhavakhiya, V. G. Synthesis of alafosfalin and its phosphinic analogue and their fungicidal activity. Mendeleev Commun. 2008, 18, 295-296.
    • (2008) Mendeleev Commun. , vol.18 , pp. 295-296
    • Khomutov, R.M.1    Osipova, T.I.2    Khurs, E.N.3    Dzhavakhiya, V.G.4
  • 76
    • 0025895388 scopus 로고
    • Preparation of N-acylated phosphonopeptides with free phosphonic group
    • Solodenko, V.; Kasheva, T.; Kukhar, V. P. Preparation of N-acylated phosphonopeptides with free phosphonic group. Synth. Commun. 1991, 21, 1631-1641.
    • (1991) Synth. Commun. , vol.21 , pp. 1631-1641
    • Solodenko, V.1    Kasheva, T.2    Kukhar, V.P.3
  • 77
    • 0024843404 scopus 로고
    • Stereoselective papain-catalyzed synthesis of alafosfalin
    • Solodenko, V. A.; Kukhar, V. P. Stereoselective papain-catalyzed synthesis of alafosfalin. Tetrahedron Lett. 1989, 30, 6917-6918.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6917-6918
    • Solodenko, V.A.1    Kukhar, V.P.2
  • 79
    • 0016422783 scopus 로고
    • Synthesis and antimicrobial evaluation of N-D-alanyl-1-aminoethylphosphonic acid
    • Huber, III, J. W.; Gilmore, W. F. Synthesis and antimicrobial evaluation of N-D-alanyl-1-aminoethylphosphonic acid. J. Med. Chem. 1975, 18, 106-108.
    • (1975) J. Med. Chem. , vol.18 , pp. 106-108
    • Huber III, J.W.1    Gilmore, W.F.2
  • 80
    • 0023764098 scopus 로고
    • Inhibition of alanine racemase by alanine phosphonate: Detection of an imine linkage to pyridoxal 5'-phosphate in the enzyme-inhibitor complex by solid-state nitrogen-15 nuclear magnetic resonance
    • Copie, V.; Faraci, W. S.; Walsh, C. T.; Griffin, R. G. Inhibition of alanine racemase by alanine phosphonate: detection of an imine linkage to pyridoxal 5'-phosphate in the enzyme-inhibitor complex by solid-state nitrogen-15 nuclear magnetic resonance. Biochemistry 1988, 27, 4966-4970.
    • (1988) Biochemistry , vol.27 , pp. 4966-4970
    • Copie, V.1    Faraci, W.S.2    Walsh, C.T.3    Griffin, R.G.4
  • 82
    • 0022577081 scopus 로고
    • Synthesis and structureactivity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
    • Atherton, F. R.; Hassall, C. H.; Lambert, R. W. Synthesis and structureactivity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. J. Med. Chem. 1986, 29, 29-40.
    • (1986) J. Med. Chem. , vol.29 , pp. 29-40
    • Atherton, F.R.1    Hassall, C.H.2    Lambert, R.W.3
  • 86
    • 0028113292 scopus 로고
    • Phase II trial of fotemustine in patients with metastatic malignant melanoma
    • Falkson, C. I.; Falkson, G.; Falkson, H. C. Phase II trial of fotemustine in patients with metastatic malignant melanoma. Invest. News Drugs 1994, 12, 251-254.
    • (1994) Invest. News Drugs , vol.12 , pp. 251-254
    • Falkson, C.I.1    Falkson, G.2    Falkson, H.C.3
  • 87
    • 0029877012 scopus 로고    scopus 로고
    • Molecular mechanisms of toxic effects of fotemustine in rat hepatocytes and subcellular rat liver fractions
    • Brakenhoff, J. P. G.; Commandeur, J. N. M.; Wormhoudt, L. W.; Groot, E. J.; Vermeulen, N. P. E. Molecular mechanisms of toxic effects of fotemustine in rat hepatocytes and subcellular rat liver fractions. Carcinogenesis 1996, 17, 715-724.
    • (1996) Carcinogenesis , vol.17 , pp. 715-724
    • Brakenhoff, J.P.G.1    Commandeur, J.N.M.2    Wormhoudt, L.W.3    Groot, E.J.4    Vermeulen, N.P.E.5
  • 88
    • 0029994657 scopus 로고    scopus 로고
    • Pharmacokinetics and pharmacodynamics of nitrosourea fotemustine: A French cancer centre multicentric study
    • Iliadis, A.; Launay-Iliadis, M.-C.; Lucas, C.; Fety, R.; Lokiec, F.; Tranchand, B.; Milano, G. Pharmacokinetics and pharmacodynamics of nitrosourea fotemustine: a French cancer centre multicentric study. Eur. J. Cancer 1996, 32A, 455-460.
    • (1996) Eur. J. Cancer , vol.32 A , pp. 455-460
    • Iliadis, A.1    Launay-Iliadis, M.-C.2    Lucas, C.3    Fety, R.4    Lokiec, F.5    Tranchand, B.6    Milano, G.7
  • 89
    • 0037108173 scopus 로고    scopus 로고
    • Aminophosphonate inhibitors of dialkylglycine decarboxylase: Structural basis for slow binding inhibition
    • Liu, W.; Rogers, C. J.; Fisher, A. J.; Toney, M. D. Aminophosphonate inhibitors of dialkylglycine decarboxylase: structural basis for slow binding inhibition. Biochemistry 2002, 41, 12320-12328.
    • (2002) Biochemistry , vol.41 , pp. 12320-12328
    • Liu, W.1    Rogers, C.J.2    Fisher, A.J.3    Toney, M.D.4
  • 90
    • 0021928231 scopus 로고
    • Purification of an alanine racemase from Streptococcus faecalis and analysis of its inactivation by (1-aminoethyl)phosphonic acid enantiomers
    • Badet, B.; Walsh, C. Purification of an alanine racemase from Streptococcus faecalis and analysis of its inactivation by (1-aminoethyl)phosphonic acid enantiomers. Biochemistry 1985, 24, 1333-1341.
    • (1985) Biochemistry , vol.24 , pp. 1333-1341
    • Badet, B.1    Walsh, C.2
  • 91
    • 0037041183 scopus 로고    scopus 로고
    • 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition
    • Auberson, Y. P.; Allgeier, H.; Bischoff, S.; Lingenhoehl, K.; Moretti, R.; Schmutz, M. 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition. Bioorg. Med. Chem. Lett. 2002, 12, 1099-1102.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1099-1102
    • Auberson, Y.P.1    Allgeier, H.2    Bischoff, S.3    Lingenhoehl, K.4    Moretti, R.5    Schmutz, M.6
  • 93
    • 0032793783 scopus 로고    scopus 로고
    • Differential in vitro association of vinca alkaloid-induced tubulin spiral filaments into aggregated spirals
    • Verdier-Pinard, P.; Garès, M.; Wright, M. Differential in vitro association of vinca alkaloid-induced tubulin spiral filaments into aggregated spirals. Biochem. Pharmacol. 1999, 58, 959-971.
    • (1999) Biochem. Pharmacol. , vol.58 , pp. 959-971
    • Verdier-Pinard, P.1    Garès, M.2    Wright, M.3
  • 94
    • 84987480058 scopus 로고
    • Nucleophilic additions to N-glycosylnitrones: Asymmetric synthesis of α-aminophosphonic acids
    • Huber, R.; Knierzinger, A.; Obrecht, J.-P.; Vasella, A. Nucleophilic additions to N-glycosylnitrones: asymmetric synthesis of α-aminophosphonic acids. Helv. Chim. Acta 1985, 68, 1730-1747.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 1730-1747
    • Huber, R.1    Knierzinger, A.2    Obrecht, J.-P.3    Vasella, A.4
  • 95
    • 0024835884 scopus 로고
    • Preparation of optically active 1-aminoalkylphosphonic acids from chiral carbamates and chiral ureas
    • Oshikawa, T.; Yamashita, M. Preparation of optically active 1-aminoalkylphosphonic acids from chiral carbamates and chiral ureas. Bull. Chem. Soc. Jpn. 1989, 62, 3177-3181.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 3177-3181
    • Oshikawa, T.1    Yamashita, M.2
  • 96
    • 0001195570 scopus 로고    scopus 로고
    • Asymmetric synthesis of α-aminophosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines
    • Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. Asymmetric synthesis of α-aminophosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines. J. Org. Chem. 1996, 61, 3687-3693.
    • (1996) J. Org. Chem. , vol.61 , pp. 3687-3693
    • Maury, C.1    Gharbaoui, T.2    Royer, J.3    Husson, H.-P.4
  • 97
    • 84985225807 scopus 로고
    • Asymmetrische synthese von (S)-(1-aminoalkyl)phosphonsäure-diethylestern unter verwendung von (+)-campher als chiralem hilfsreagens
    • Schöllkopf, U.; Schütze, R. Asymmetrische synthese von (S)-(1-aminoalkyl)phosphonsäure-diethylestern unter verwendung von (+)-campher als chiralem hilfsreagens. Liebigs Ann. Chem. 1987, 45-49.
    • (1987) Liebigs Ann. Chem. , pp. 45-49
    • Schöllkopf, U.1    Schütze, R.2
  • 98
    • 0026663281 scopus 로고
    • A simple and general method for the asymmetric synthesis of α-aminophosphonic acids
    • Maury, C.; Royer, J.; Husson, H.-P. A simple and general method for the asymmetric synthesis of α-aminophosphonic acids. Tetrahedron Lett. 1992, 33, 6127-6130.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6127-6130
    • Maury, C.1    Royer, J.2    Husson, H.-P.3
  • 99
    • 0025187520 scopus 로고
    • A versatile asymmetric synthesis of α-amino α-alkylphosphonic acids of high enantiomeric purity
    • Hanessian, S.; Bennani, Y. L. A versatile asymmetric synthesis of α-amino α-alkylphosphonic acids of high enantiomeric purity. Tetrahedron Lett. 1990, 31, 6465-6468.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6465-6468
    • Hanessian, S.1    Bennani, Y.L.2
  • 100
    • 30744461593 scopus 로고    scopus 로고
    • Facile and efficient asymmetric synthesis of α-aminoalkylphosphonic acids
    • Yuan, C.-Y.; Chen, Q.-Y. Facile and efficient asymmetric synthesis of α-aminoalkylphosphonic acids. Chin. J. Chem. 2005, 23, 1671-1676.
    • (2005) Chin. J. Chem. , vol.23 , pp. 1671-1676
    • Yuan, C.-Y.1    Chen, Q.-Y.2
  • 101
    • 0036020828 scopus 로고    scopus 로고
    • Asymmetric synthesis of aminophosphonic acids and trifluoromethylated derivatives thereof
    • Yuan, C.-Y.; Li, J. X.; Cui, S.; Wang, G. Asymmetric synthesis of aminophosphonic acids and trifluoromethylated derivatives thereof. Phosphorus Sulfur 2002, 177, 1731-1734.
    • (2002) Phosphorus Sulfur , vol.177 , pp. 1731-1734
    • Yuan, C.-Y.1    Li, J.X.2    Cui, S.3    Wang, G.4
  • 102
    • 0026516860 scopus 로고
    • Recent advances in the Staudinger reaction
    • Gololobov, Y. G.; Kasukhin, L. F. Recent advances in the Staudinger reaction. Tetrahedron 1992, 48, 1353-1406.
    • (1992) Tetrahedron , vol.48 , pp. 1353-1406
    • Gololobov, Y.G.1    Kasukhin, L.F.2
  • 103
    • 3042698861 scopus 로고    scopus 로고
    • Mechanisms of Staudinger reactions within density functional theory
    • and references cited therein
    • Tian, W. Q.; Wang, Y. A. Mechanisms of Staudinger reactions within density functional theory. J. Org. Chem. 2004, 69, 4299-4308 and references cited therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 4299-4308
    • Tian, W.Q.1    Wang, Y.A.2
  • 104
    • 0034499739 scopus 로고    scopus 로고
    • A new and efficient asymmetric synthesis of 1-amino-1-alkylphosphonic acids
    • Yuan, C.; Li, S.; Wang, G. A new and efficient asymmetric synthesis of 1-amino-1-alkylphosphonic acids. Heteroatom. Chem. 2000, 11, 528-535.
    • (2000) Heteroatom. Chem. , vol.11 , pp. 528-535
    • Yuan, C.1    Li, S.2    Wang, G.3
  • 105
    • 84986691327 scopus 로고
    • Phosphoranalogue von aminosäuren III. Synthese optisch aktiver 1-aminoalkylphosphonsäuren der (S)-und (R)-reihe mit hilfe von (-)-ephedrin als auxiliar
    • Sting, M.; Steglich, W. Phosphoranalogue von aminosäuren III. Synthese optisch aktiver 1-aminoalkylphosphonsäuren der (S)-und (R)-reihe mit hilfe von (-)-ephedrin als auxiliar. Synthesis 1990, 132-134.
    • (1990) Synthesis , pp. 132-134
    • Sting, M.1    Steglich, W.2
  • 106
    • 0028618170 scopus 로고
    • Electrophilic amination and azidation of chiral α-alkyl phosphonamides: Asymmetric syntheses of α-amino α-alkyl phosphonic acids
    • Hanessian, S.; Bennani, Y. F. Electrophilic amination and azidation of chiral α-alkyl phosphonamides: asymmetric syntheses of α-amino α-alkyl phosphonic acids. Synthesis 1994, 1272-1274.
    • (1994) Synthesis , pp. 1272-1274
    • Hanessian, S.1    Bennani, Y.F.2
  • 107
    • 0001551678 scopus 로고    scopus 로고
    • Synthesis of α-amino phosphonic acids by asymmetric hydrogenation
    • Kitamura, M.; Yoshimura, M.; Tsukamoto, M.; Noyori, R. Synthesis of α-amino phosphonic acids by asymmetric hydrogenation. Enantiomer 1996, 1, 281-303.
    • (1996) Enantiomer , vol.1 , pp. 281-303
    • Kitamura, M.1    Yoshimura, M.2    Tsukamoto, M.3    Noyori, R.4
  • 108
    • 84985186249 scopus 로고
    • Enantioselective synthesis of L-(1-aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation of N-[1-(dimethoxy-phosphoryl)ethenyl]formamide
    • Schöllkopf, U.; Hoppe, I.; Thiele, A. Enantioselective synthesis of L-(1-aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation of N-[1-(dimethoxy-phosphoryl)ethenyl]formamide. Liebigs Ann. Chem. 1985, 555-559.
    • (1985) Liebigs Ann. Chem. , pp. 555-559
    • Schöllkopf, U.1    Hoppe, I.2    Thiele, A.3
  • 109
    • 0018745481 scopus 로고
    • Phosphonopeptides as antibacterial agents: Rationale, chemistry, and structure-activity relationships
    • Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Lambert, R. W.; Ringrose, P. S. Phosphonopeptides as antibacterial agents: rationale, chemistry, and structure-activity relationships. Antimicrob. Agents Chemother. 1979, 15, 677-683.
    • (1979) Antimicrob. Agents Chemother. , vol.15 , pp. 677-683
    • Atherton, F.R.1    Hall, M.J.2    Hassall, C.H.3    Lambert, R.W.4    Ringrose, P.S.5
  • 110
    • 0000726942 scopus 로고
    • Optically active 1-aminoalkanephosphonic acids. Dibenzoyl-L-tartaric anhydride as an effective agent for the resolution of racemic diphenyl 1-aminoalkanephosphonates
    • Kafarski, P.; Lejczak, B.; Szewczyk, J. Optically active 1-aminoalkanephosphonic acids. Dibenzoyl-L-tartaric anhydride as an effective agent for the resolution of racemic diphenyl 1-aminoalkanephosphonates. Can. J. Chem. 1983, 61, 2425-2030.
    • (1983) Can. J. Chem. , vol.61 , pp. 2030-2425
    • Kafarski, P.1    Lejczak, B.2    Szewczyk, J.3
  • 111
    • 0343449134 scopus 로고
    • Determination of absolute configuration of optically active 1-aminoalkanephosphonic acids by chemical correlations
    • Kowalik, J.; Zygmunt, J.; Mastalerz, P. Determination of absolute configuration of optically active 1-aminoalkanephosphonic acids by chemical correlations. Phosphorus Sulfur 1983, 18, 393-396.
    • (1983) Phosphorus Sulfur , vol.18 , pp. 393-396
    • Kowalik, J.1    Zygmunt, J.2    Mastalerz, P.3
  • 112
    • 13344267040 scopus 로고
    • Chromatographic assigment of the configuration of 1-aminoalkanephosphonic acids
    • Lejczak, B.; Kafarski, P.; Mastalerz, P. Chromatographic assigment of the configuration of 1-aminoalkanephosphonic acids. J. Chromatogr. A 1985, 324, 455-461.
    • (1985) J. Chromatogr. A , vol.324 , pp. 455-461
    • Lejczak, B.1    Kafarski, P.2    Mastalerz, P.3
  • 113
    • 0025843366 scopus 로고
    • Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective anzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids
    • Solodenko, V. A.; Kasheva, T. N.; Kukhar, V. P.; Kozlova, E. V.; Mironenko, D. A.; Vedas, V. K. Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective anzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids. Tetrahedron 1991, 47, 3989-3998.
    • (1991) Tetrahedron , vol.47 , pp. 3989-3998
    • Solodenko, V.A.1    Kasheva, T.N.2    Kukhar, V.P.3    Kozlova, E.V.4    Mironenko, D.A.5    Vedas, V.K.6
  • 116
    • 2342618859 scopus 로고    scopus 로고
    • Development of irreversible diphenyl phosphonate inhibitors for urokinase plasminogen activator
    • Joossens, J.; Van der Veken, P.; Lambeir, A.-M.; Augustyns, K.; Haemers, A. Development of irreversible diphenyl phosphonate inhibitors for urokinase plasminogen activator. J. Med. Chem. 2004, 47, 2411-2413.
    • (2004) J. Med. Chem. , vol.47 , pp. 2411-2413
    • Joossens, J.1    van der Veken, P.2    Lambeir, A.-M.3    Augustyns, K.4    Haemers, A.5
  • 117
    • 0022200175 scopus 로고
    • In the search for new anticancer drugs. 13. Phosphonic and phosphinic analogues of ornithine
    • Sosnovsky, G.; Lukszo, J.; Gravela, E.; Zuretti, M. F. In the search for new anticancer drugs. 13. Phosphonic and phosphinic analogues of ornithine. J. Med. Chem. 1985, 28, 1350-1354.
    • (1985) J. Med. Chem. , vol.28 , pp. 1350-1354
    • Sosnovsky, G.1    Lukszo, J.2    Gravela, E.3    Zuretti, M.F.4
  • 118
    • 0027230517 scopus 로고
    • A convenient synthesis of N-protected diphenyl phosphonate ester analogues of ornithine, lysine and homolysine
    • Hamilton, R.; Walker, B. J.; Walker, B. A convenient synthesis of N-protected diphenyl phosphonate ester analogues of ornithine, lysine and homolysine. Tetrahedron Lett. 1993, 34, 2847-2850.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2847-2850
    • Hamilton, R.1    Walker, B.J.2    Walker, B.3
  • 121
    • 0242575091 scopus 로고    scopus 로고
    • Utilisation of structurally diverse organophosphonates by Streptomycetes
    • Obojska, A.; Lejczak, B. Utilisation of structurally diverse organophosphonates by Streptomycetes. Appl. Microbiol. Biotechnol. 2003, 62, 557-563.
    • (2003) Appl. Microbiol. Biotechnol. , vol.62 , pp. 557-563
    • Obojska, A.1    Lejczak, B.2
  • 122
    • 33847660883 scopus 로고    scopus 로고
    • Isolation and characterization of two new microbial strains capable of degradation of the naturally occurring organophosphonate-ciliatine
    • Klimeck-Ochab, M.; Obojska, A.; Lejczak, B.; Picco, A. N. Isolation and characterization of two new microbial strains capable of degradation of the naturally occurring organophosphonate-ciliatine. Biodegradation 2007, 18, 223-231.
    • (2007) Biodegradation , vol.18 , pp. 223-231
    • Klimeck-Ochab, M.1    Obojska, A.2    Lejczak, B.3    Picco, A.N.4
  • 123
    • 84985087355 scopus 로고
    • Asymmetric synthesis of α-aminophosphonic acids by cycloaddition of N-glycosyl-C-dialkoxyphosphonoylnitrones
    • Vasella, A.; Voeffray, R. Asymmetric synthesis of α-aminophosphonic acids by cycloaddition of N-glycosyl-C-dialkoxyphosphonoylnitrones. Helv. Chim. Acta 1982, 65, 1953-1964.
    • (1982) Helv. Chim. Acta , vol.65 , pp. 1953-1964
    • Vasella, A.1    Voeffray, R.2
  • 124
    • 0019958810 scopus 로고
    • Aminophosphonic and aminophosphinic acid analogues of aspartic acid
    • Campell, M. M.; Carruthers, N. I.; Mickel, S. J. Aminophosphonic and aminophosphinic acid analogues of aspartic acid. Tetrahedron 1982, 38, 2513-2524.
    • (1982) Tetrahedron , vol.38 , pp. 2513-2524
    • Campell, M.M.1    Carruthers, N.I.2    Mickel, S.J.3
  • 125
    • 37049104232 scopus 로고
    • Synthesis of α-aminophosphonic and α-aminophosphinic acids and derived dipeptides from 4-acetoxyazetidin-2-ones
    • Campell, M. M.; Carruthers, N. I. Synthesis of α-aminophosphonic and α-aminophosphinic acids and derived dipeptides from 4-acetoxyazetidin-2-ones. J. Chem. Soc., Chem. Commun. 1980, 730-731.
    • (1980) J. Chem. Soc., Chem. Commun. , pp. 730-731
    • Campell, M.M.1    Carruthers, N.I.2
  • 126
    • 0032493326 scopus 로고    scopus 로고
    • Synthesis and proteinase inhibitory properties of diphenyl phosphonate analogues of aspartic and glutamic acids
    • Hamilton, R.; Walker, B.; Walker, B. J. Synthesis and proteinase inhibitory properties of diphenyl phosphonate analogues of aspartic and glutamic acids. Bioorg. Med. Chem. Lett. 1998, 9, 1655-1660.
    • (1998) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1655-1660
    • Hamilton, R.1    Walker, B.2    Walker, B.J.3
  • 127
    • 0022408355 scopus 로고
    • N-(Phosphonoacetyl)amino phosphonates Phosphonate analogues of N (phosphonoacetyl)-L-aspartic acid (PALA)
    • Kafarski, P.; Lejczak, B.; Mastalerz, P.; Du, D.; Radzikowski, C. N-(Phosphonoacetyl)amino phosphonates. Phosphonate analogues of N (phosphonoacetyl)-L-aspartic acid (PALA). J. Med. Chem. 1995, 28, 1555-1558.
    • (1995) J. Med. Chem. , vol.28 , pp. 1555-1558
    • Kafarski, P.1    Lejczak, B.2    Mastalerz, P.3    Du, D.4    Radzikowski, C.5
  • 128
    • 0027433691 scopus 로고
    • Inhibition of aminopeptidases by phosphonic acid and phosphinic acid analogues of aspartic and glutamic acids
    • Lejczak, B.; Popiel de Choszczak, M.; Kafarski, P. Inhibition of aminopeptidases by phosphonic acid and phosphinic acid analogues of aspartic and glutamic acids. J. Enzyme Inhib. Med. Chem. 1993, 7, 97-103.
    • (1993) J. Enzyme Inhib. Med. Chem. , vol.7 , pp. 97-103
    • Lejczak, B.1    Popiel de Choszczak, M.2    Kafarski, P.3
  • 129
    • 84989719185 scopus 로고
    • Herbicidal activity of phosphonic and phosphinic acid analogues of glutamic and aspartic acids
    • Miliszkiewicz, D.; Wieczorek, P.; Lejczak, B.; Kowalik, E.; Kafarski, P. Herbicidal activity of phosphonic and phosphinic acid analogues of glutamic and aspartic acids. Pestic. Sci. 1992, 34, 349-354.
    • (1992) Pestic. Sci. , vol.34 , pp. 349-354
    • Miliszkiewicz, D.1    Wieczorek, P.2    Lejczak, B.3    Kowalik, E.4    Kafarski, P.5
  • 130
    • 0009225758 scopus 로고
    • Complexes of aminophosphonates. II Transition metal complexes of aminophosphonic acid analogues of aspartic acid and glutamic acid
    • Kiss, T.; Farkas, E. Complexes of aminophosphonates. II. Transition metal complexes of aminophosphonic acid analogues of aspartic acid and glutamic acid. Inorg. Chim. Acta 1989, 155, 281-287.
    • (1989) Inorg. Chim. Acta , vol.155 , pp. 281-287
    • Kiss, T.1    Farkas, E.2
  • 131
    • 84986374290 scopus 로고
    • Phosphonocysteine and phosphonohomocysteine; synthesis and isolation
    • Kudzin, Z. H. Phosphonocysteine and phosphonohomocysteine; synthesis and isolation. Synthesis 1983, 812-813.
    • (1983) Synthesis , pp. 812-813
    • Kudzin, Z.H.1
  • 132
    • 0001523922 scopus 로고
    • Aziridine-2-phosphonic acid, the valuable synthon for synthesis of 1-amino-2-functionalized ethanephosphonic acids
    • Zygmunt, J. Aziridine-2-phosphonic acid, the valuable synthon for synthesis of 1-amino-2-functionalized ethanephosphonic acids. Tetrahedron 1985, 41, 4979-4982.
    • (1985) Tetrahedron , vol.41 , pp. 4979-4982
    • Zygmunt, J.1
  • 133
    • 5144221294 scopus 로고
    • 1-Amino-2-mercaptoethanephosphonic acid, the phosphonic analog of cysteine
    • Kowalik, J.; Zygmunt, J.; Mastalerz, P. 1-Amino-2-mercaptoethanephosphonic acid, the phosphonic analog of cysteine. Pol. J. Chem. 1981, 55, 713-715.
    • (1981) Pol. J. Chem. , vol.55 , pp. 713-715
    • Kowalik, J.1    Zygmunt, J.2    Mastalerz, P.3
  • 134
    • 5144221340 scopus 로고    scopus 로고
    • Optically active diethyl N-(ptoluenesulfonyl)-aziridine-2-phosphonates as chiral synthons for the synthesis of γ-substituted ω-aminophosphonates
    • Dolence, E. K.; Roylance, J. B. Optically active diethyl N-(ptoluenesulfonyl)-aziridine-2-phosphonates as chiral synthons for the synthesis of γ-substituted ω-aminophosphonates. Tetrahedron: Asymmetry 2004, 15, 3307-3322.
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3307-3322
    • Dolence, E.K.1    Roylance, J.B.2
  • 135
    • 0019881070 scopus 로고
    • Inhibition of rat liver glutamine synthetase by phosphonic analogues of glutamic acid
    • Lejczak, B.; Starzemska, H.; Mastalerz, P. Inhibition of rat liver glutamine synthetase by phosphonic analogues of glutamic acid. Experientia 1981, 37, 461-462.
    • (1981) Experientia , vol.37 , pp. 461-462
    • Lejczak, B.1    Starzemska, H.2    Mastalerz, P.3
  • 136
    • 0002157166 scopus 로고
    • Organische phosphorverbindungen 79 herstellung und eigenschaften von ω-amino-carboxyalkylphosphon-und-phosphinsäuren
    • Diel, P. J.; Maier, L. Organische phosphorverbindungen 79 herstellung und eigenschaften von ω-amino-carboxyalkylphosphon-und-phosphinsäuren. Phosphorus Sulfur 1987, 29, 201-209.
    • (1987) Phosphorus Sulfur , vol.29 , pp. 201-209
    • Diel, P.J.1    Maier, L.2
  • 137
    • 0030713348 scopus 로고    scopus 로고
    • A tyrosine residue essential for catalytic activity in aminopeptidase A
    • Vazeux, G.; Iturrioz, X.; Corvol, P.; Llorens-Cortès, C. A tyrosine residue essential for catalytic activity in aminopeptidase A. Biochem. J. 1997, 327, 883-889.
    • (1997) Biochem. J. , vol.327 , pp. 883-889
    • Vazeux, G.1    Iturrioz, X.2    Corvol, P.3    Llorens-Cortès, C.4
  • 138
    • 0029609299 scopus 로고
    • Enantioselective synthesis of diverse ω-aminophosphonate diesters
    • Smith, III, A. B.; Yager, K. M.; Taylor, C. M. Enantioselective synthesis of diverse ω-aminophosphonate diesters. J. Am. Chem. Soc. 1995, 117, 10879-10888.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10879-10888
    • Smith III, A.B.1    Yager, K.M.2    Taylor, C.M.3
  • 140
    • 0028898313 scopus 로고
    • ω-Aminophosphonate derivatives as nucleophiles in diastereoselective and enantioselective palladium catalysed allylic substitution reactions
    • For the catalytic enantioselective synthesis of ω-aminophosphonates from 92, see
    • For the catalytic enantioselective synthesis of ω-aminophosphonates from 92, see: Baldwin, I. C.; Williams, J. M. J.; Beckett, R. P. ω-Aminophosphonate derivatives as nucleophiles in diastereoselective and enantioselective palladium catalysed allylic substitution reactions. Tetrahedron: Asymmetry 1995, 6, 679-682.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 679-682
    • Baldwin, I.C.1    Williams, J.M.J.2    Beckett, R.P.3
  • 141
    • 3543122090 scopus 로고
    • Separation of racemic phosphonic analogues of glutamic acid
    • Antczak, K.; Szewczyk, J. Separation of racemic phosphonic analogues of glutamic acid. Phosphorus Sulfur 1985, 22, 247-251.
    • (1985) Phosphorus Sulfur , vol.22 , pp. 247-251
    • Antczak, K.1    Szewczyk, J.2
  • 142
    • 0020406531 scopus 로고
    • New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate
    • For the synthesis of 100, see
    • For the synthesis of 100, see: Oleksyszyn, J.; Gruszecka, E.; Kafarski, P.; Mastalerz, P. New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate. Monatsh. Chem. 1982, 113, 59-71.
    • (1982) Monatsh. Chem. , vol.113 , pp. 59-71
    • Oleksyszyn, J.1    Gruszecka, E.2    Kafarski, P.3    Mastalerz, P.4
  • 143
    • 0028258788 scopus 로고
    • 1-Amino-2-imidazol-4'-ylethylphosphonic acid is a potent reversible inhibitor of Pseudomonas putida histidine ammonia-lyase
    • Hernandez, D.; Phillips, A. T.; Zon, J. 1-Amino-2-imidazol-4'-ylethylphosphonic acid is a potent reversible inhibitor of Pseudomonas putida histidine ammonia-lyase. Biochem. Mol. Biol. Int. 1994, 32, 189-194.
    • (1994) Biochem. Mol. Biol. Int. , vol.32 , pp. 189-194
    • Hernandez, D.1    Phillips, A.T.2    Zon, J.3
  • 144
    • 0042572071 scopus 로고
    • ω-Amino-(4-imidazoil)-ethylphosphonic acid, the phosphonoisostere of histidine
    • Wu, Y. Y.-L.; Tishler, M. ω-Amino-(4-imidazoil)-ethylphosphonic acid, the phosphonoisostere of histidine. Chin. Chem. Lett. 1991, 2, 95-98.
    • (1991) Chin. Chem. Lett. , vol.2 , pp. 95-98
    • Wu, Y.Y.-L.1    Tishler, M.2
  • 145
    • 0027174063 scopus 로고
    • Inhibitory effect of synthetic aminophosphonic acid derivatives on human carbonic anhydrase
    • Ösapay, G.; Csiba, A. Inhibitory effect of synthetic aminophosphonic acid derivatives on human carbonic anhydrase. Eur. J. Med. Chem. 1993, 28, 355-361.
    • (1993) Eur. J. Med. Chem. , vol.28 , pp. 355-361
    • Ösapay, G.1    Csiba, A.2
  • 146
    • 50949112789 scopus 로고    scopus 로고
    • Chemical target validation studies of aminopeptidase in malaria parasites using ω-aminoalkylphosphonate and phosphonopeptide inhibitors
    • Cunningham, E.; Drag, M.; Kafarski, P.; Bell, A. Chemical target validation studies of aminopeptidase in malaria parasites using ω-aminoalkylphosphonate and phosphonopeptide inhibitors. Antimicrob. Agents Chemother. 2008, 52, 3221-3228.
    • (2008) Antimicrob. Agents Chemother. , vol.52 , pp. 3221-3228
    • Cunningham, E.1    Drag, M.2    Kafarski, P.3    Bell, A.4
  • 147
    • 0033532313 scopus 로고    scopus 로고
    • Enzymes in organic chemistry Part 9: Chemo-enzymatic synthesis of phosphonic acid analogues of L-valine, Lleucine, L-isoleucine, L-methionine and L-ω-aminobutyric acid of high enantiomeric excess
    • Hammerschmidt, F.; Wuggenig, F. Enzymes in organic chemistry. Part 9: chemo-enzymatic synthesis of phosphonic acid analogues of L-valine, Lleucine, L-isoleucine, L-methionine and L-ω-aminobutyric acid of high enantiomeric excess. Tetrahedron: Asymmetry 1999, 10, 1709-1721.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 1709-1721
    • Hammerschmidt, F.1    Wuggenig, F.2
  • 148
    • 0028960436 scopus 로고
    • Enzymes in organic chemistry, part 2: Lipase-catalysed hydrolysis of 1-acyloxy-2-aryethylphosphonates and synthesis of phosphonic acid analogues of L-phenylalanine and L-tyrosine
    • Drescher, M.; Li, Y.-F.; Hammerschmidt, F. Enzymes in organic chemistry, part 2: lipase-catalysed hydrolysis of 1-acyloxy-2-aryethylphosphonates and synthesis of phosphonic acid analogues of L-phenylalanine and L-tyrosine. Tetrahedron 1995, 51, 4933-4946.
    • (1995) Tetrahedron , vol.51 , pp. 4933-4946
    • Drescher, M.1    Li, Y.-F.2    Hammerschmidt, F.3
  • 149
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 150
    • 0002779608 scopus 로고
    • Replacement of alcoholic hydroxyl groups by halogens and other nucleophiles via oxyphosphonium intermediates
    • Castro, B. R. Replacement of alcoholic hydroxyl groups by halogens and other nucleophiles via oxyphosphonium intermediates. Org. React. 1983, 29, 1-162.
    • (1983) Org. React. , vol.29 , pp. 1-162
    • Castro, B.R.1
  • 151
    • 0000414496 scopus 로고
    • The Mitsunobu reaction
    • Hughess, D. L. The Mitsunobu reaction. Org. React. 1992, 42, 335-356.
    • (1992) Org. React. , vol.42 , pp. 335-356
    • Hughess, D.L.1
  • 152
    • 0001640928 scopus 로고    scopus 로고
    • Progress in the Mitsunobu reaction A review
    • Hughess, D. L. Progress in the Mitsunobu reaction. A review. Org. Prep. Proced. Int. 1996, 28, 127-164.
    • (1996) Org. Prep. Proced. Int. , vol.28 , pp. 127-164
    • Hughess, D.L.1
  • 153
    • 0001088596 scopus 로고    scopus 로고
    • Advances in the Mitsunobu reaction for the stereochemical inversion of hindered secondary alcohols
    • Dodge, J. A.; Jones, S. A. Advances in the Mitsunobu reaction for the stereochemical inversion of hindered secondary alcohols. Rec. Res. Dev. Org. Chem. 1997, 1, 273-283.
    • (1997) Rec. Res. Dev. Org. Chem. , vol.1 , pp. 273-283
    • Dodge, J.A.1    Jones, S.A.2
  • 154
    • 4143084064 scopus 로고    scopus 로고
    • Recent advances in the Mitsunobu reaction: Modified reagents and the quest for chromatography-free separation
    • Dembinski, R. Recent advances in the Mitsunobu reaction: modified reagents and the quest for chromatography-free separation. Eur. J. Org. Chem. 2004, 2763-2772.
    • (2004) Eur. J. Org. Chem. , pp. 2763-2772
    • Dembinski, R.1
  • 155
    • 0037071231 scopus 로고    scopus 로고
    • Fluorous Mitsunobu reagents and reactions
    • Dandapani, S.; Curran, D. P. Fluorous Mitsunobu reagents and reactions. Tetrahedron 2002, 58, 3855-3864.
    • (2002) Tetrahedron , vol.58 , pp. 3855-3864
    • Dandapani, S.1    Curran, D.P.2
  • 156
    • 33750902195 scopus 로고    scopus 로고
    • Simplification of the Mitsunobu reaction Di-p-chlorobenzyl azodicarboxylate: A new azodicarboxylate
    • Lipshutz, B. H.; Chung, D. W.; Rich, B.; Corral, R. Simplification of the Mitsunobu reaction. Di-p-chlorobenzyl azodicarboxylate: a new azodicarboxylate. Org. Lett. 2006, 8, 5069-5072.
    • (2006) Org. Lett. , vol.8 , pp. 5069-5072
    • Lipshutz, B.H.1    Chung, D.W.2    Rich, B.3    Corral, R.4
  • 157
    • 0037467898 scopus 로고    scopus 로고
    • A convenient synthesis of 1-aminophosphonates from 1-hydroxyphosphonates
    • For the synthesis of non-chiral ω-aminophosphonates from ω-hydroxyphosphonates under solvent-free conditions using microwave irradiation, see
    • For the synthesis of non-chiral ω-aminophosphonates from ω-hydroxyphosphonates under solvent-free conditions using microwave irradiation, see: Kaboudin, B. A convenient synthesis of 1-aminophosphonates from 1-hydroxyphosphonates. Tetrahedron Lett. 2003, 44, 1051-1053.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1051-1053
    • Kaboudin, B.1
  • 158
    • 23944516347 scopus 로고    scopus 로고
    • ω-Aminoalkylphosphonates as a tool in experimental optimisation of P1 side chain shape of potential inhibitors in S1 pocket of leucine-and neutral aminopeptidases
    • Drαg, M.; Grembecka, J.; Paweαczak, M.; Kafarski, P. ω-Aminoalkylphosphonates as a tool in experimental optimisation of P1 side chain shape of potential inhibitors in S1 pocket of leucine-and neutral aminopeptidases. Eur. J. Med. Chem. 2005, 40, 764-771.
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 764-771
    • Drαg, M.1    Grembecka, J.2    Paweαczak, M.3    Kafarski, P.4
  • 159
    • 0035912827 scopus 로고    scopus 로고
    • Inhibition of the aminopeptidase from Aeromonas proteolytica by L-leucinephosphonic acid Spectroscopic and crystallographic characterization of the transition state of peptide hydrolysis
    • Stamper, C.; Bennett, B.; Edwards, T.; Holz, R. C.; Ringe, D.; Petsko, G. Inhibition of the aminopeptidase from Aeromonas proteolytica by L-leucinephosphonic acid. Spectroscopic and crystallographic characterization of the transition state of peptide hydrolysis. Biochemistry 2001, 40, 7035-7046.
    • (2001) Biochemistry , vol.40 , pp. 7035-7046
    • Stamper, C.1    Bennett, B.2    Edwards, T.3    Holz, R.C.4    Ringe, D.5    Petsko, G.6
  • 160
    • 0141649386 scopus 로고    scopus 로고
    • A new enzyme model for enantioselective esterases based on molecularly imprinted polymers
    • Emgenbroich, M.; Wulff, G. A new enzyme model for enantioselective esterases based on molecularly imprinted polymers. Chem. Eur. J. 2003, 9, 4106-4117.
    • (2003) Chem. Eur. J. , vol.9 , pp. 4106-4117
    • Emgenbroich, M.1    Wulff, G.2
  • 161
    • 0038115341 scopus 로고    scopus 로고
    • The most potent organophosphorus inhibitors of leucine aminopeptidase Structure-based design, chemistry, and activity
    • Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity. J. Med. Chem. 2003, 46, 2641-2655.
    • (2003) J. Med. Chem. , vol.46 , pp. 2641-2655
    • Grembecka, J.1    Mucha, A.2    Cierpicki, T.3    Kafarski, P.4
  • 162
    • 0032567158 scopus 로고    scopus 로고
    • Inhibition of the aminopeptidase from Aeromonas proteolytica by L-leucinephosphonic acid, a transition state analogue of peptide hydrolysis
    • Bennett, B.; Holz, R. C. Inhibition of the aminopeptidase from Aeromonas proteolytica by L-leucinephosphonic acid, a transition state analogue of peptide hydrolysis. J. Am. Chem. Soc. 1998, 120, 12139-12140.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 12139-12140
    • Bennett, B.1    Holz, R.C.2
  • 163
    • 0029025424 scopus 로고
    • A highly convenient route to optically pure ω-aminophosphonic acids
    • Hamilton, R.; Walker, B.; Walker, B. J. A highly convenient route to optically pure ω-aminophosphonic acids. Tetrahedron Lett. 1995, 36, 4451-4454.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4451-4454
    • Hamilton, R.1    Walker, B.2    Walker, B.J.3
  • 164
    • 0036020811 scopus 로고    scopus 로고
    • The computer-aided design, synthesis, and activity prediction of new leucine aminopeptidase inhibitors
    • Drag, M.; Grembecka, J.; Kafarski, P. The computer-aided design, synthesis, and activity prediction of new leucine aminopeptidase inhibitors. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 1591-1595.
    • (2002) Phosphorus, Sulfur Silicon Relat. Elem. , vol.177 , pp. 1591-1595
    • Drag, M.1    Grembecka, J.2    Kafarski, P.3
  • 165
    • 1842555199 scopus 로고    scopus 로고
    • Thiourea-catalyzed enantioselective hydrophosphonylation of imines: Practical access to enantiomerically enriched ω-amino phosphonic acids
    • Joly, G. D.; Jacobsen, E. N. Thiourea-catalyzed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched ω-amino phosphonic acids. J. Am. Chem. Soc. 2004, 126, 4102-4103.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 4102-4103
    • Joly, G.D.1    Jacobsen, E.N.2
  • 166
    • 0026551174 scopus 로고
    • Enantioselective synthesis of ω-aminophosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphite
    • Yokomatsu, T.; Shibuya, S. Enantioselective synthesis of ω-aminophosphonic acids by an application of stereoselective opening of homochiral dioxane acetals with triethyl phosphite. Tetrahedron: Asymmetry 1992, 3, 377-378.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 377-378
    • Yokomatsu, T.1    Shibuya, S.2
  • 167
    • 0032543521 scopus 로고    scopus 로고
    • Synthesis and evaluation of diphenyl phosphonate esters as inhibitors of the trypsin-like granzymes A and K and mast cell tryptase
    • Jackson, D. S.; Fraser, S. A.; Ni, L.-M.; Kam, C.-M.; Winkler, U.; Johnson, D. A.; Froelich, C. J.; Hudig, D.; Powers, J. C. Synthesis and evaluation of diphenyl phosphonate esters as inhibitors of the trypsin-like granzymes A and K and mast cell tryptase. J. Med. Chem. 1998, 41, 2289-2301.
    • (1998) J. Med. Chem. , vol.41 , pp. 2289-2301
    • Jackson, D.S.1    Fraser, S.A.2    Ni, L.-M.3    Kam, C.-M.4    Winkler, U.5    Johnson, D.A.6    Froelich, C.J.7    Hudig, D.8    Powers, J.C.9
  • 169
    • 0034512642 scopus 로고    scopus 로고
    • Syntheses of new racemic N-(1-iminoethyl)phosphalysine derivatives as potential inhibitors of nitric oxide synthase
    • Massa, M. A.; Pitzele, B. S.; Jerome, G. M.; Moore, W. M.; Manning, P. T.; Sikorski, J. A. Syntheses of new racemic N-(1-iminoethyl)phosphalysine derivatives as potential inhibitors of nitric oxide synthase. Heteroatom Chem. 2000, 11, 505-511.
    • (2000) Heteroatom Chem. , vol.11 , pp. 505-511
    • Massa, M.A.1    Pitzele, B.S.2    Jerome, G.M.3    Moore, W.M.4    Manning, P.T.5    Sikorski, J.A.6
  • 170
    • 0013610276 scopus 로고
    • 1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids
    • Keith, B. E.; Campbell, C. D.; Dingwall, J. G. 1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids. J. Chem. Soc., Perkin Trans. 1 1984, 2845-2853.
    • (1984) J. Chem. Soc., Perkin Trans. 1 , pp. 2845-2853
    • Keith, B.E.1    Campbell, C.D.2    Dingwall, J.G.3
  • 172
    • 33646513265 scopus 로고    scopus 로고
    • Synthesis of isocyanide derivatives of ω-aminoalkylphosphonate diphenyl esters
    • For the synthesis of protected LysP, see
    • For the synthesis of protected LysP, see: Sieβczyk, M.; Kliszczak, M.; Oleksyszyn, J. Synthesis of isocyanide derivatives of ω-aminoalkylphosphonate diphenyl esters. Tetrahedron Lett. 2006, 47, 4209-4211.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 4209-4211
    • Sießczyk, M.1    Kliszczak, M.2    Oleksyszyn, J.3
  • 173
    • 0033539594 scopus 로고    scopus 로고
    • Insights into the mechanism of Escherichia coli methionine aminopeptidase from the structural analysis of reaction products and phosphorus-based transition-state analogues
    • Lowther, W. T.; Zhang, Y.; Sampson, P. B.; Honek, J. F.; Matthews, B. W. Insights into the mechanism of Escherichia coli methionine aminopeptidase from the structural analysis of reaction products and phosphorus-based transition-state analogues. Biochemistry 1999, 38, 14810-14819.
    • (1999) Biochemistry , vol.38 , pp. 14810-14819
    • Lowther, W.T.1    Zhang, Y.2    Sampson, P.B.3    Honek, J.F.4    Matthews, B.W.5
  • 174
    • 0031571612 scopus 로고    scopus 로고
    • Synthesis and kinetic studies of diphenyl 1-(N-peptidylamino)alkanephosphonate esters and their biotinylated derivatives as inhibitors of serine proteases and probes for lymphocyte granzymes
    • Abuelyaman, A. S.; Jackson, D. S.; Hudig, D.; Woodard, S. L.; Powers, J. C. Synthesis and kinetic studies of diphenyl 1-(N-peptidylamino)alkanephosphonate esters and their biotinylated derivatives as inhibitors of serine proteases and probes for lymphocyte granzymes. Arch. Biochem. Biophys. 1997, 344, 271-280.
    • (1997) Arch. Biochem. Biophys. , vol.344 , pp. 271-280
    • Abuelyaman, A.S.1    Jackson, D.S.2    Hudig, D.3    Woodard, S.L.4    Powers, J.C.5
  • 175
    • 0028512603 scopus 로고
    • Fluorescent derivatives of diphenyl[1-(Npeptidylamino) alkyl]phosphonate esters: Synthesis and use in the inhibition and cellular localization of serine proteases
    • Abuelyaman, A. S.; Hudig, D.; Woodard, S. L.; Powers, J. C. Fluorescent derivatives of diphenyl[1-(Npeptidylamino) alkyl]phosphonate esters: synthesis and use in the inhibition and cellular localization of serine proteases. Bioconjugate Chem. 1994, 5, 400-405.
    • (1994) Bioconjugate Chem. , vol.5 , pp. 400-405
    • Abuelyaman, A.S.1    Hudig, D.2    Woodard, S.L.3    Powers, J.C.4
  • 176
    • 0025979246 scopus 로고
    • Irreversible inhibition of serine proteases by peptide derivatives of (ω-aminoalkyl)phosphonate diphenyl esters
    • Oleksyszyn, J.; Powers, J. C. Irreversible inhibition of serine proteases by peptide derivatives of (ω-aminoalkyl)phosphonate diphenyl esters. Biochemistry 1991, 30, 485-493.
    • (1991) Biochemistry , vol.30 , pp. 485-493
    • Oleksyszyn, J.1    Powers, J.C.2
  • 177
    • 0037059912 scopus 로고    scopus 로고
    • Synthesis of an ω-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase
    • Steere, J. A.; Sampson, P. B.; Honek, J. F. Synthesis of an ω-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase. Bioorg. Med. Chem. Lett. 2002, 12, 457-460.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 457-460
    • Steere, J.A.1    Sampson, P.B.2    Honek, J.F.3
  • 178
    • 0001357755 scopus 로고
    • Nucleophilic additions to N-glycosylnitrones: Asymmetric synthesis of N-hydroxy-ω-aminophosphonic and ω-aminophosphonic acids
    • Huber, R.; Vasella, A. Nucleophilic additions to N-glycosylnitrones: asymmetric synthesis of N-hydroxy-ω-aminophosphonic and ω-aminophosphonic acids. Helv. Chim. Acta 1987, 70, 1461-1476.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 1461-1476
    • Huber, R.1    Vasella, A.2
  • 179
    • 0019545487 scopus 로고
    • Dual effects of phenylalanine analogs on rabbit-muscle pyruvate kinase activity
    • Izbicka-Dimitrjevic, E.; Mastalerz, P.; Kochman, M. Dual effects of phenylalanine analogs on rabbit-muscle pyruvate kinase activity. Eur. J. Biochem. 1981, 114, 565-568.
    • (1981) Eur. J. Biochem. , vol.114 , pp. 565-568
    • Izbicka-Dimitrjevic, E.1    Mastalerz, P.2    Kochman, M.3
  • 180
    • 0030272641 scopus 로고    scopus 로고
    • Phosphatase inhibitors-III Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase
    • Beers, S. A.; Schwender, C. F.; Loughney, D. A.; Malloy, E.; Demarest, K.; Jordan, J. Phosphatase inhibitors-III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase. Bioorg. Med. Chem. 1996, 4, 1693-1701.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 1693-1701
    • Beers, S.A.1    Schwender, C.F.2    Loughney, D.A.3    Malloy, E.4    Demarest, K.5    Jordan, J.6
  • 181
    • 84963145245 scopus 로고
    • Organic phosphorus compounds Synthesis and properties of 1-amino-2-arylethylphosphonic and phosphinic acids as well as phosphine oxides
    • Maier, L. Organic phosphorus compounds. Synthesis and properties of 1-amino-2-arylethylphosphonic and phosphinic acids as well as phosphine oxides. Phosphorus Sulfur 1990, 53, 43-67.
    • (1990) Phosphorus Sulfur , vol.53 , pp. 43-67
    • Maier, L.1
  • 182
    • 0029929790 scopus 로고    scopus 로고
    • Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity
    • Wagner, J.; Lerner, R. A.; Barbas, III, C. F. Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity. Bioorg. Med. Chem. 1996, 4, 901-916.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 901-916
    • Wagner, J.1    Lerner, R.A.2    Barbas III, C.F.3
  • 183
    • 0030598676 scopus 로고    scopus 로고
    • Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11
    • McKittrick, B. A.; Stamford, A. W.; Weng, X.; Ma, K.; Chackalamannil, S.; Czarniecki, M.; Cleven, R. M.; Fawzi, A. B. Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11. Bioorg. Med. Chem. Lett. 1996, 6, 1629-1634.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1629-1634
    • McKittrick, B.A.1    Stamford, A.W.2    Weng, X.3    Ma, K.4    Chackalamannil, S.5    Czarniecki, M.6    Cleven, R.M.7    Fawzi, A.B.8
  • 184
    • 0026438772 scopus 로고
    • Synthesis of stereochemically defined phosphonamidate-containing peptides: Inhibitors for the HIV-1 proteinase
    • Camp, N. P.; Hawkins, P. C. D.; Hitchcock, P. B.; Gani, D. Synthesis of stereochemically defined phosphonamidate-containing peptides: inhibitors for the HIV-1 proteinase. Bioorg. Med. Chem. Lett. 1992, 2, 1047-1050.
    • (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 1047-1050
    • Camp, N.P.1    Hawkins, P.C.D.2    Hitchcock, P.B.3    Gani, D.4
  • 185
    • 0032236435 scopus 로고    scopus 로고
    • Synthesis of phosphono dipeptides, inhibitors of cathepsin C
    • Pawelczak, M.; Nowak, K.; Kafarski, P. Synthesis of phosphono dipeptides, inhibitors of cathepsin C. Phosphorus Sulfur 1998, 132, 65-71.
    • (1998) Phosphorus Sulfur , vol.132 , pp. 65-71
    • Pawelczak, M.1    Nowak, K.2    Kafarski, P.3
  • 186
    • 0037169268 scopus 로고    scopus 로고
    • Chymase inhibitor suppresses adhesion formation in a hamster experimental model
    • Okamoto, Y.; Takai, S.; Miyazaki, M. Chymase inhibitor suppresses adhesion formation in a hamster experimental model. Eur. J. Pharmacol. 2002, 435, 265-267.
    • (2002) Eur. J. Pharmacol. , vol.435 , pp. 265-267
    • Okamoto, Y.1    Takai, S.2    Miyazaki, M.3
  • 188
    • 0034194353 scopus 로고    scopus 로고
    • A one-pot multistep approach to γ-azidophosphonate and phosphonothioate diesters: Key intermediates in the synthesis of haptens for the generation of antibody ligases
    • Harwig, C. W.; Hoffman, T. Z.; Wentworth, A. D.; Janda, K. D. A one-pot multistep approach to γ-azidophosphonate and phosphonothioate diesters: key intermediates in the synthesis of haptens for the generation of antibody ligases. Bioorg. Med. Chem. Lett. 2000, 10, 915-918.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 915-918
    • Harwig, C.W.1    Hoffman, T.Z.2    Wentworth, A.D.3    Janda, K.D.4
  • 189
    • 0021749522 scopus 로고
    • Phosphorous-containing analogues of aspartame
    • Nelson, V.; Mastalerz, P. Phosphorous-containing analogues of aspartame. J. Pharm. Sci. 1984, 73, 1844-1846.
    • (1984) J. Pharm. Sci. , vol.73 , pp. 1844-1846
    • Nelson, V.1    Mastalerz, P.2
  • 190
    • 52749098178 scopus 로고    scopus 로고
    • Stereoselective synthesis of enantiopure cyclic γ-aminophosphonic acids: Direct observation of inversion at phosphorus in phosphonate ester silyldealkylation by bromotrimethylsilane
    • For diastereoselectivity explication, see
    • For diastereoselectivity explication, see: Alfonsov, V. A.; McKenna, C. E.; Bayandina, E. V.; Kashemirov, B. A.; Yarmieva, L. N.; Punegova, L. N.; Kataeva, O. N. Stereoselective synthesis of enantiopure cyclic γ-aminophosphonic acids: direct observation of inversion at phosphorus in phosphonate ester silyldealkylation by bromotrimethylsilane. Heteroatom. Chem. 2008, 19, 575-582.
    • (2008) Heteroatom. Chem. , vol.19 , pp. 575-582
    • Alfonsov, V.A.1    McKenna, C.E.2    Bayandina, E.V.3    Kashemirov, B.A.4    Yarmieva, L.N.5    Punegova, L.N.6    Kataeva, O.N.7
  • 192
    • 0024544078 scopus 로고
    • Asymmetric synthesis of (1-aminoalkyl)phosphonic acids via asymmetric aldol reaction of (isocyanomethyl) phosphonates catalyzed by a chiral ferrocenyl-phosphine-gold(I) complex
    • Sawamura, M.; Ito, Y.; Hayashi, T. Asymmetric synthesis of (1-aminoalkyl)phosphonic acids via asymmetric aldol reaction of (isocyanomethyl) phosphonates catalyzed by a chiral ferrocenyl-phosphine-gold(I) complex. Tetrahedron Lett. 1989, 30, 2247-2250.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2247-2250
    • Sawamura, M.1    Ito, Y.2    Hayashi, T.3
  • 193
    • 0029929790 scopus 로고    scopus 로고
    • Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity
    • Wagner, J.; Lerner, R. A.; Barbas, III, C. F. Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity. Bioorg. Med. Chem. 1996, 4, 901-916.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 901-916
    • Wagner, J.1    Lerner, R.A.2    Barbas III, C.F.3
  • 194
    • 37049105484 scopus 로고
    • Synthesis, molecular structure, and absolute configuration of an optically active (1-amino-2-phenylethyl)phosphonic acid monohydrate
    • Kowalik, J.; Sawka-Dobrowolska, W.; Gβowiak, T. Synthesis, molecular structure, and absolute configuration of an optically active (1-amino-2-phenylethyl)phosphonic acid monohydrate. J. Chem. Soc., Chem. Commun. 1984, 446-447.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 446-447
    • Kowalik, J.1    Sawka-Dobrowolska, W.2    Gßowiak, T.3
  • 196
    • 33744814981 scopus 로고    scopus 로고
    • Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: Towards syn selectivity in the presence of Lewis bases
    • Dinér, P.; Amedjkouh, M. Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases. Org. Biomol. Chem. 2006, 4, 2091-2096.
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 2091-2096
    • Dinér, P.1    Amedjkouh, M.2
  • 197
    • 58649104900 scopus 로고    scopus 로고
    • Asymmetric conjugate addition of unmodified cyclic ketones to nitroolefins using aminophosphonate as the organocatalyst
    • Chen, G.; Wang, Z.; Ding, K. Asymmetric conjugate addition of unmodified cyclic ketones to nitroolefins using aminophosphonate as the organocatalyst. Chin. J. Chem. 2009, 27, 163-168.
    • (2009) Chin. J. Chem. , vol.27 , pp. 163-168
    • Chen, G.1    Wang, Z.2    Ding, K.3
  • 198
    • 45849103527 scopus 로고    scopus 로고
    • γ-Aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins
    • Tao, Q.; Tang, G.; Lin, K.; Zhao, Y.-F. γ-Aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins. Chirality 2008, 20, 833-838.
    • (2008) Chirality , vol.20 , pp. 833-838
    • Tao, Q.1    Tang, G.2    Lin, K.3    Zhao, Y.-F.4
  • 199
    • 50649112343 scopus 로고    scopus 로고
    • Asymmetric conjugate addition of nitroalkanes to enones with a chiral γ-aminophosphonate catalyst
    • Malmgren, M.; Granander, J.; Amedjkouh, M. Asymmetric conjugate addition of nitroalkanes to enones with a chiral γ-aminophosphonate catalyst. Tetrahedron: Asymmetry 2008, 19, 1934-1940.
    • (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1934-1940
    • Malmgren, M.1    Granander, J.2    Amedjkouh, M.3
  • 200
    • 25444463074 scopus 로고    scopus 로고
    • Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand
    • Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand. J. Org. Chem. 2005, 70, 8107-8109.
    • (2005) J. Org. Chem. , vol.70 , pp. 8107-8109
    • Rao, H.1    Fu, H.2    Jiang, Y.3    Zhao, Y.4
  • 203
  • 206
    • 0001356419 scopus 로고
    • Synthesis of 2-phosphonopyrrolidine and its substitution for proline in an inhibitor of angiotensin-converting enzyme
    • Petrillo, Jr., E. W.; Spitzmiller, E. R. Synthesis of 2-phosphonopyrrolidine and its substitution for proline in an inhibitor of angiotensin-converting enzyme. Tetrahedron Lett. 1979, 4929-4930.
    • (1979) Tetrahedron Lett. , pp. 4929-4930
    • Petrillo Jr., E.W.1    Spitzmiller, E.R.2
  • 207
    • 0021793924 scopus 로고
    • Synthesis and biological activity of carboxylic acid replacement analogues of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline
    • Almquist, R. G.; Chao, W.-R.; Jennings-White, C. Synthesis and biological activity of carboxylic acid replacement analogues of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline. J. Med. Chem. 1985, 28, 1067-1071.
    • (1985) J. Med. Chem. , vol.28 , pp. 1067-1071
    • Almquist, R.G.1    Chao, W.-R.2    Jennings-White, C.3
  • 208
    • 37049166036 scopus 로고
    • A synthesis of tropinone
    • Robinson, R. A synthesis of tropinone. J. Chem. Soc. 1917, 111, 762-768.
    • (1917) J. Chem. Soc. , vol.111 , pp. 762-768
    • Robinson, R.1
  • 209
    • 0001519457 scopus 로고
    • Die synthese von naturstoffen, insbesondere von alkaloiden, unter physiolo-gischen
    • Schopf, C. Die synthese von naturstoffen, insbesondere von alkaloiden, unter physiolo-gischen. Angew. Chem. 1937, 50, 779-787.
    • (1937) Angew. Chem. , vol.50 , pp. 779-787
    • Schopf, C.1
  • 210
    • 0000566807 scopus 로고
    • Stereochemistry of the Robinson-Schoepf reaction A stereospecific total synthesis of the ladybug defense alkaloids precoccinelline and coccinelline
    • Stevens, R. V.; Lee, A. W. M. Stereochemistry of the Robinson-Schoepf reaction. A stereospecific total synthesis of the ladybug defense alkaloids precoccinelline and coccinelline. J. Am. Chem. Soc. 1979, 101, 7032-7035.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 7032-7035
    • Stevens, R.V.1    Lee, A.W.M.2
  • 211
    • 56949105334 scopus 로고    scopus 로고
    • A stable chiral 1,4-dihydropyridine equivalent for the asymmetric synthesis of substituted piperidines: 2-cyano-6-phenyl-oxazolopiperidine
    • Bonin, M.; Grierson, D. S.; Royer, J.; Husson H.-P. A stable chiral 1,4-dihydropyridine equivalent for the asymmetric synthesis of substituted piperidines: 2-cyano-6-phenyl-oxazolopiperidine. Org. Synth. Coll. 1998, 9, 176-180.
    • (1998) Org. Synth. Coll. , vol.9 , pp. 176-180
    • Bonin, M.1    Grierson, D.S.2    Royer, J.3    Husson, H.-P.4
  • 212
    • 0033583019 scopus 로고    scopus 로고
    • Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3S,5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine
    • Katritzky, A. R.; Cui, X.-L.; Yang, B.; Steel, P. J. Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3S,5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine. J. Org. Chem. 1999, 64, 1979-1985.
    • (1999) J. Org. Chem. , vol.64 , pp. 1979-1985
    • Katritzky, A.R.1    Cui, X.-L.2    Yang, B.3    Steel, P.J.4
  • 213
    • 0035795103 scopus 로고    scopus 로고
    • Synthesis of novel (R)-and (S)-piperidazine-3-phosphonic acids and transformation into (R)-and (S)-pyrrolidine-2-phosphonic acids
    • Kaname, M.; Arakawa, Y.; Yoshifuji, S. Synthesis of novel (R)-and (S)-piperidazine-3-phosphonic acids and transformation into (R)-and (S)-pyrrolidine-2-phosphonic acids. Tetrahedron Lett. 2001, 42, 2713-2716.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2713-2716
    • Kaname, M.1    Arakawa, Y.2    Yoshifuji, S.3
  • 214
    • 67650745031 scopus 로고    scopus 로고
    • Potential neuroprotective drugs in cerebral ischemia: New saturated and polyunsaturated lipids coupled to hydrophilic moieties: Synthesis and biological activity
    • Biraboneye, A. C.; Madonna, S.; Laras, Y.; Krantic, S.; Maher, P.; Kraus, J.-L. Potential neuroprotective drugs in cerebral ischemia: new saturated and polyunsaturated lipids coupled to hydrophilic moieties: synthesis and biological activity. J. Med. Chem. 2009, 52, 4358-4369.
    • (2009) J. Med. Chem. , vol.52 , pp. 4358-4369
    • Biraboneye, A.C.1    Madonna, S.2    Laras, Y.3    Krantic, S.4    Maher, P.5    Kraus, J.-L.6
  • 216
    • 84986704022 scopus 로고
    • Absolute konfiguration der (2-amino-1-hydroxyethyl) phosphon-säure aus Acanthamoeba castellanii (Neff)-darstellung der phosphonsäure-analoga von (+)-und (-)-serin
    • Hammerschmidt, F.; Völlenkle, H. Absolute konfiguration der (2-amino-1-hydroxyethyl) phosphon-säure aus Acanthamoeba castellanii (Neff)-darstellung der phosphonsäure-analoga von (+)-und (-)-serin. Liebigs Ann. Chem. 1989, 577-583.
    • (1989) Liebigs Ann. Chem. , pp. 577-583
    • Hammerschmidt, F.1    Völlenkle, H.2
  • 217
    • 0034725687 scopus 로고    scopus 로고
    • Enzymes in organic chemistry Part 10: Chemo-enzymatic synthesis of L-phosphaserine and L-phosphaisoserine and enantioseparation of aminohydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent
    • Hammerschmidt, F.; Lindner, W.; Wuggenig, F.; Zarbl, E. Enzymes in organic chemistry. Part 10: chemo-enzymatic synthesis of L-phosphaserine and L-phosphaisoserine and enantioseparation of aminohydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent. Tetrahedron: Asymmetry 2000, 11, 2955-2964.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 2955-2964
    • Hammerschmidt, F.1    Lindner, W.2    Wuggenig, F.3    Zarbl, E.4
  • 218
    • 0000033249 scopus 로고
    • γ-Alkylation of serine with self-reproduction of the center of chirality
    • Seebach, D.; Aebi, J. D. γ-Alkylation of serine with self-reproduction of the center of chirality. Tetrahedron Lett. 1984, 25, 2545-2548.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2545-2548
    • Seebach, D.1    Aebi, J.D.2
  • 219
    • 84985571847 scopus 로고
    • Preparation of chiral building blocks from amino acids and peptides via electrolytic decarboxylation and TiCl4-induced aminoalkylation
    • Renaud, P.; Seebach, D. Preparation of chiral building blocks from amino acids and peptides via electrolytic decarboxylation and TiCl4-induced aminoalkylation. Angew. Chem. Int. Ed. Engl. 1986, 25, 843-844.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 843-844
    • Renaud, P.1    Seebach, D.2
  • 221
    • 0029903192 scopus 로고    scopus 로고
    • Efficient synthesis of the four diastereomers of phosphothreonine from lactaldehyde
    • Bongini, A.; Camerini, R.; Panunzio, M. Efficient synthesis of the four diastereomers of phosphothreonine from lactaldehyde. Tetrahedron: Asymmetry 1996, 7, 1467-1476.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1467-1476
    • Bongini, A.1    Camerini, R.2    Panunzio, M.3
  • 222
    • 0027949155 scopus 로고
    • Synthesis of (1S,2S)-phosphothreonine via Ntrimethylsilylimine of (S)-lactic aldehyde
    • Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Synthesis of (1S,2S)-phosphothreonine via Ntrimethylsilylimine of (S)-lactic aldehyde. Tetrahedron Lett. 1994, 35, 8045-8048.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8045-8048
    • Bongini, A.1    Camerini, R.2    Hofman, S.3    Panunzio, M.4
  • 223
    • 85047671655 scopus 로고
    • Asymmetric synthesis of γ-amino α-hydroxy phosphonic acids via BINAP-ruthenium catalyzed hydrogenation
    • Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Asymmetric synthesis of γ-amino α-hydroxy phosphonic acids via BINAP-ruthenium catalyzed hydrogenation. Tetrahedron Lett. 1995, 36, 5769-5772.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5769-5772
    • Kitamura, M.1    Tokunaga, M.2    Pham, T.3    Lubell, W.D.4    Noyori, R.5
  • 224
    • 84986409622 scopus 로고
    • 50 Elektrochemische decarboxylierung von L-threonin-und oligopeptidderivaten unter bildung von N-acyl-N, O-acetalen: Herstellung von oligopeptiden mit carboxamid-oder phosphonat-C-terminus
    • Seebach, D.; Charczuk, R.; Geber, C.; Renaud, P.; Berner, H.; Schneider, H. 50. Elektrochemische decarboxylierung von L-threonin-und oligopeptidderivaten unter bildung von N-acyl-N, O-acetalen: herstellung von oligopeptiden mit carboxamid-oder phosphonat-C-terminus. Helv. Chim. Acta 1989, 72, 401-425.
    • (1989) Helv. Chim. Acta , vol.72 , pp. 401-425
    • Seebach, D.1    Charczuk, R.2    Geber, C.3    Renaud, P.4    Berner, H.5    Schneider, H.6
  • 226
    • 0036520839 scopus 로고    scopus 로고
    • Computational study of the catalytic domain of human neutrophil collagenase Specific role of the S3 and S'3 subsites in the interaction with a phosphonate inhibitor
    • Aschi, M.; Roccatano, D.; Di Nola, A.; Gallina, C.; Gavuzzo, E.; Pochetti, G.; Pieper, M.; Tschesche, H.; Mazza, F. Computational study of the catalytic domain of human neutrophil collagenase. Specific role of the S3 and S'3 subsites in the interaction with a phosphonate inhibitor. J. Comput.-Aided Mol. Des. 2002, 16, 213-225.
    • (2002) J. Comput.-Aided Mol. Des. , vol.16 , pp. 213-225
    • Aschi, M.1    Roccatano, D.2    Di Nola, A.3    Gallina, C.4    Gavuzzo, E.5    Pochetti, G.6    Pieper, M.7    Tschesche, H.8    Mazza, F.9
  • 228
    • 0034618636 scopus 로고    scopus 로고
    • Two crystal structures of human neutrophil collagenase, one complexed with a primed-and the other with an unprimed-side inhibitor: Implications for drug design
    • Gavuzzo, E.; Pochetti, G.; Mazza, F.; Gallina, C.; Gorini, B.; D'Alessio, S.; Pieper, M.; Tschesche, H.; Tucker, P. A. Two crystal structures of human neutrophil collagenase, one complexed with a primed-and the other with an unprimed-side inhibitor: implications for drug design. J. Med. Chem. 2000, 43, 3377-3385.
    • (2000) J. Med. Chem. , vol.43 , pp. 3377-3385
    • Gavuzzo, E.1    Pochetti, G.2    Mazza, F.3    Gallina, C.4    Gorini, B.5    D'Alessio, S.6    Pieper, M.7    Tschesche, H.8    Tucker, P.A.9
  • 229
    • 85064410120 scopus 로고
    • An improved synthesis of the phosphonic acid analog of tryptophan
    • Rogers, R. S.; Sterm, M. K. An improved synthesis of the phosphonic acid analog of tryptophan. Synlett 1992, 708-708.
    • (1992) Synlett , pp. 708
    • Rogers, R.S.1    Sterm, M.K.2
  • 230
    • 0001877222 scopus 로고
    • The synthesis of D, L-phosphotryptophan
    • Chen, S. F.; Kumar, S. D.; Tishler, M. The synthesis of D, L-phosphotryptophan. Tetrahedron Lett. 1983, 24, 5461-5464.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5461-5464
    • Chen, S.F.1    Kumar, S.D.2    Tishler, M.3
  • 232
    • 0021224327 scopus 로고
    • Isolation and characterization of I5B2, a new phosphorus containing inhibitor of angiotensin I converting enzyme produced by Actinomadura sp
    • Kido, Y.; Hamakado, T.; Anno, M.; Miyagawa, E.; Motoki, Y.; Wakamiya, T.; Shiba, T. Isolation and characterization of I5B2, a new phosphorus containing inhibitor of angiotensin I converting enzyme produced by Actinomadura sp. J. Antibiot. 1984, 37, 965-969.
    • (1984) J. Antibiot. , vol.37 , pp. 965-969
    • Kido, Y.1    Hamakado, T.2    Anno, M.3    Miyagawa, E.4    Motoki, Y.5    Wakamiya, T.6    Shiba, T.7
  • 233
    • 43549111368 scopus 로고    scopus 로고
    • Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26
    • Ntai, I.; Bachmann, B. O. Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26. Bioorg. Med. Chem. Lett. 2008, 18, 3068-3071.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 3068-3071
    • Ntai, I.1    Bachmann, B.O.2
  • 234
    • 33750440778 scopus 로고    scopus 로고
    • Phosphonopeptide K-26 biosynthetic intermediates in Astrosporangium hypotensionis
    • Ntai, I.; Vanessa V. Phelan, V. V.; Bachmann, B. O. Phosphonopeptide K-26 biosynthetic intermediates in Astrosporangium hypotensionis. Chem. Commun. 2006, 4518-4520.
    • (2006) Chem. Commun. , pp. 4518-4520
    • Ntai, I.1    Vanessa, V.2    Phelan, V.V.3    Bachmann, B.O.4
  • 236
    • 0025890985 scopus 로고
    • Structure and conformation of a novel inhibitor of angiotensin I converting enzyme: A tripeptide containing phosphonic acid
    • Hirayama, N.; Kasai, M.; Shirahata, K. Structure and conformation of a novel inhibitor of angiotensin I converting enzyme: a tripeptide containing phosphonic acid. Int. J. Pept. Prot. Res. 1991, 38, 20-24.
    • (1991) Int. J. Pept. Prot. Res. , vol.38 , pp. 20-24
    • Hirayama, N.1    Kasai, M.2    Shirahata, K.3
  • 237
    • 0343449134 scopus 로고
    • Determination of absolute configuration of optically active 1-aminoalkanephosphonic acids by chemical correlations
    • Kowalik, J.; Zygmunt, J.; Mastalerz, P. Determination of absolute configuration of optically active 1-aminoalkanephosphonic acids by chemical correlations. Phosphorus Sulfur 1983, 18, 393-396.
    • (1983) Phosphorus Sulfur , vol.18 , pp. 393-396
    • Kowalik, J.1    Zygmunt, J.2    Mastalerz, P.3
  • 238
    • 0022570993 scopus 로고
    • K-4, a novel inhibitor of angiotensin I converting enzyme produced by Actinomadura spiculosospora
    • Koguchi, T.; Yamada, K.; Yamoto, M.; Okachi, R.; Nakayama, K.; Kase, K. K-4, a novel inhibitor of angiotensin I converting enzyme produced by Actinomadura spiculosospora. J. Antibiot. 1986, 39, 364-371.
    • (1986) J. Antibiot. , vol.39 , pp. 364-371
    • Koguchi, T.1    Yamada, K.2    Yamoto, M.3    Okachi, R.4    Nakayama, K.5    Kase, K.6
  • 239
    • 0023143082 scopus 로고
    • Phosphonic analogues of tyrosine and 3,4-dihydroxyphenylalanine (dopa) influence mushroom tyrosinase activity
    • Lejczak, B.; Kafarski, P.; Makowiecka, E. Phosphonic analogues of tyrosine and 3,4-dihydroxyphenylalanine (dopa) influence mushroom tyrosinase activity. Biochem. J. 1987, 242, 81-88.
    • (1987) Biochem. J. , vol.242 , pp. 81-88
    • Lejczak, B.1    Kafarski, P.2    Makowiecka, E.3
  • 240
    • 0014189785 scopus 로고
    • Recherches sur les acides aminoalkylphosphoniques. I Action de la tyrosinase sur l'analogue phosphonique de la tyrosine
    • Cassaigne, A.; Lacoste, A. M.; Neuzil, E. Recherches sur les acides aminoalkylphosphoniques. I. Action de la tyrosinase sur l'analogue phosphonique de la tyrosine. Bull. Soc. Chim. Biol. 1967, 49, 1813-1825.
    • (1967) Bull. Soc. Chim. Biol. , vol.49 , pp. 1813-1825
    • Cassaigne, A.1    Lacoste, A.M.2    Neuzil, E.3
  • 246
    • 33751154738 scopus 로고
    • Catalytic Asymmetric Synthesis of α-aminophosphonates using lanthanoid-potassium-BINOL complexes
    • Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. Catalytic Asymmetric Synthesis of α-aminophosphonates using lanthanoid-potassium-BINOL complexes. J. Org. Chem. 1995, 60, 6656-6657.
    • (1995) J. Org. Chem. , vol.60 , pp. 6656-6657
    • Sasai, H.1    Arai, S.2    Tahara, Y.3    Shibasaki, M.4


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