메뉴 건너뛰기




Volumn 12, Issue 4, 2006, Pages 303-309

Facile synthesis of phosphonamidate- and phosphonate-linked phosphonopeptides

Author keywords

Peptide; Phosphonamidate; Phosphonate; Phosphonopeptide; Synthesis

Indexed keywords

ALDEHYDE; AMINO ACID DERIVATIVE; BENZYL DERIVATIVE; CARBAMIC ACID DERIVATIVE; ESTER DERIVATIVE; HYDROXYL GROUP; PHOSPHITE; PHOSPHONAMIDIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHOPEPTIDE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33645870163     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.727     Document Type: Article
Times cited : (19)

References (36)
  • 1
    • 0001299493 scopus 로고
    • A phosphonamidate dipeptide analog as an inhibitor of carboxypeptidase A
    • Jacobsen NE, Bartlett PA. A phosphonamidate dipeptide analog as an inhibitor of carboxypeptidase A. J. Am. Chem. Soc. 1981; 103: 654-657.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 654-657
    • Jacobsen, N.E.1    Bartlett, P.A.2
  • 3
    • 0022213778 scopus 로고
    • Synthesis and biological evaluation of phosphonamidate peptide inhibitors of enkephalinase and angiotensin-converting enzyme
    • Elliott RL, Marks N, Berg MJ, Portoghese PS. Synthesis and biological evaluation of phosphonamidate peptide inhibitors of enkephalinase and angiotensin-converting enzyme. J. Med. Chem. 1985; 28: 1208-1216.
    • (1985) J. Med. Chem. , vol.28 , pp. 1208-1216
    • Elliott, R.L.1    Marks, N.2    Berg, M.J.3    Portoghese, P.S.4
  • 4
    • 0023277991 scopus 로고
    • Phosphorus amino acid analogs as inhibitors of leucine aminopeptidase
    • Giannousis PP, Bartlett PA. Phosphorus amino acid analogs 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
  • 5
    • 0023105721 scopus 로고
    • Evaluation of intrinsic binding energy from a hydrogen bonding group in an enzyme inhibitor
    • Bartlett PA, Marlowe CK. Evaluation of intrinsic binding energy from a hydrogen bonding group in an enzyme inhibitor. Science 1987; 235: 569-571.
    • (1987) Science , vol.235 , pp. 569-571
    • Bartlett, P.A.1    Marlowe, C.K.2
  • 6
    • 0026666539 scopus 로고
    • +], a new amide bond replacement: Potent, slow-binding inhibition of the HIV protease
    • +], a new amide bond replacement: potent, slow-binding inhibition of the HIV protease. J. Am. Chem. Soc. 1992; 114: 7604-7606.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7604-7606
    • Ikeda, J.A.1    Ashley, J.A.2    Wirsching, P.3    Janda, K.D.4
  • 7
    • 0028578656 scopus 로고
    • The chemistry of phosphapeptides: Investigations on the synthesis of phosphonamidate, phosphonate, and phosphinate analogs of glutamyl-γ-glutamate
    • Malachowski WP, Coward JK. The chemistry of phosphapeptides: investigations on the synthesis of phosphonamidate, phosphonate, and phosphinate analogs of glutamyl-γ-glutamate. J. Org. Chem. 1994; 59: 7625-7634.
    • (1994) J. Org. Chem. , vol.59 , pp. 7625-7634
    • Malachowski, W.P.1    Coward, J.K.2
  • 8
    • 0034657545 scopus 로고    scopus 로고
    • Phosphonamidate and phosphothioate dipeptides as potential inhibitors of VanX
    • Yang KW, Brandt JJ, Chatwood LL, Crowder MW. Phosphonamidate and phosphothioate dipeptides as potential inhibitors of VanX. Bioorg. Med. Chem. Lett. 2000; 10: 1085-1087.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1085-1087
    • Yang, K.W.1    Brandt, J.J.2    Chatwood, L.L.3    Crowder, M.W.4
  • 9
    • 0025730616 scopus 로고
    • At the crossroads of chemistry and immunology: Catalytic antibodies
    • Lerner PA, Benkovic SJ, Schultz PG. At the crossroads of chemistry and immunology: catalytic antibodies. Science 1991: 252: 659-667.
    • (1991) Science , vol.252 , pp. 659-667
    • Lerner, P.A.1    Benkovic, S.J.2    Schultz, P.G.3
  • 11
    • 0000791343 scopus 로고
    • Antibody catalysis of difficult chemical transformations
    • Lerner RA. Antibody catalysis of difficult chemical transformations. Acc. Chem. Res. 1993; 20: 391-395.
    • (1993) Acc. Chem. Res. , vol.20 , pp. 391-395
    • Lerner, R.A.1
  • 16
    • 0028561861 scopus 로고
    • The chemistry of phosphapeptides: Formation of functionalized phosphonochloridates under mild conditions and their reaction with alcohols and amines
    • Malachowski WP, Coward JK. The chemistry of phosphapeptides: formation of functionalized phosphonochloridates under mild conditions and their reaction with alcohols and amines. J. Org. Chem. 1994; 59: 7616-6724.
    • (1994) J. Org. Chem. , vol.59 , pp. 6724-7616
    • Malachowski, W.P.1    Coward, J.K.2
  • 17
    • 0022860034 scopus 로고
    • Inhibition of chymotrypsin by phosphonate and phosphonamidate peptide analogs
    • Bartlett PA, Lamden LA. Inhibition of chymotrypsin by phosphonate and phosphonamidate peptide analogs. Bioorg. Chem. 1986; 14: 356-377.
    • (1986) Bioorg. Chem. , vol.14 , pp. 356-377
    • Bartlett, P.A.1    Lamden, L.A.2
  • 20
    • 33845278913 scopus 로고
    • Synthesis of phosphoric acid derivatives by oxidative activation of phosphinate esters
    • Sampson NS, Bartlett PA. Synthesis of phosphoric 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    Bartlett, P.A.2
  • 21
    • 0028153364 scopus 로고
    • The preparation of phosphono peptides containing a phosphonamidate bond
    • Mucha A, Kafarski P, Plenat F, Cristau H-J. The preparation of phosphono peptides containing a phosphonamidate bond. Tetrahedron 1994; 50: 12743-12754.
    • (1994) Tetrahedron , vol.50 , pp. 12743-12754
    • Mucha, A.1    Kafarski, P.2    Plenat, F.3    Cristau, H.-J.4
  • 22
    • 0028884444 scopus 로고
    • Synthesis of phosphonate and thiophosphonate esters and amides from hydrogen-phosphinates by a novel one-pot activation-coupling-oxidation procedure
    • de Fatima Fernandez M, Vlaar CP, Fan H, Liu YH, Fronczek FR, Hammer RP. Synthesis of phosphonate and thiophosphonate esters and amides from hydrogen-phosphinates by a novel one-pot activation-coupling-oxidation procedure. J. Org. Chem. 1995; 60: 7390-7391.
    • (1995) J. Org. Chem. , vol.60 , pp. 7390-7391
    • de Fatima Fernandez, M.1    Vlaar, C.P.2    Fan, H.3    Liu, Y.H.4    Fronczek, F.R.5    Hammer, R.P.6
  • 23
    • 0000420816 scopus 로고
    • (1H-Benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate- and (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate-mediated activation of monophosphonate esters: Synthesis of mixed phosphonate diesters, the reactivity of the benzotriazolyl phosphonic esters vs the reactivity of the benzotriazolyl carboxylic esters
    • Campagne J-M, Coste J, Jouin P. (1H-Benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate- and (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate-mediated activation of monophosphonate esters: synthesis of mixed phosphonate diesters, the reactivity of the benzotriazolyl phosphonic esters vs the reactivity of the benzotriazolyl carboxylic esters. J. Org. Chem. 1995; 60: 5214-5223.
    • (1995) J. Org. Chem. , vol.60 , pp. 5214-5223
    • Campagne, J.-M.1    Coste, J.2    Jouin, P.3
  • 24
    • 0016176481 scopus 로고
    • New compounds: Monoesters of α-aminobenzylphosphonic acid
    • Gilmore WF, Mc Bridge HAJ. New compounds: monoesters of α-aminobenzylphosphonic acid. J. Pharm. Sci. 1974; 63: 965-966.
    • (1974) J. Pharm. Sci. , vol.63 , pp. 965-966
    • Gilmore, W.F.1    Mc Bridge, H.A.J.2
  • 25
    • 0027377987 scopus 로고
    • Synthesis of mixed phosphonate diester analogs of dipeptides using BOP or PYBOP reagents
    • Campagne J-M, Coste J, Jouin P. Synthesis of mixed phosphonate diester analogs of dipeptides using BOP or PYBOP reagents. Tetrahedron Lett. 1993: 34: 6743-6744.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6743-6744
    • Campagne, J.-M.1    Coste, J.2    Jouin, P.3
  • 26
    • 0026093346 scopus 로고
    • Differential binding energy: A detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorous-containing inhibitors
    • Morgan BP, Scholtz JM, Ballinger MD, Zipkin ID, Bartlett PA. Differential binding energy: a detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorous-containing inhibitors. J. Am. Chem. Soc. 1991; 113: 297-307.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 297-307
    • Morgan, B.P.1    Scholtz, J.M.2    Ballinger, M.D.3    Zipkin, I.D.4    Bartlett, P.A.5
  • 27
    • 0030012630 scopus 로고    scopus 로고
    • A straightforward synthesis of α-amino phosphate monoesters using BroP or TPyClU
    • Galeotti N, Coste J, Bedos P, Jouin P. A straightforward synthesis of α-amino phosphate monoesters using BroP or TPyClU. Tetrahedron Lett. 1996; 37: 3997-3998.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3997-3998
    • Galeotti, N.1    Coste, J.2    Bedos, P.3    Jouin, P.4
  • 28
    • 0000651698 scopus 로고
    • The synthesis of phosphonate esters; an extension of the Mitsunobu reaction
    • Campbell DA. The synthesis of phosphonate esters; an extension of the Mitsunobu reaction. J. Org. Chem. 1992; 57: 6331-6335.
    • (1992) J. Org. Chem. , vol.57 , pp. 6331-6335
    • Campbell, D.A.1
  • 29
    • 0028326599 scopus 로고
    • Phosphonate ester synthesis using a modified Mitsunobu condensation
    • Campbell DA, Bermak JC. Phosphonate ester synthesis using a modified Mitsunobu condensation. J. Org. Chem. 1994; 59: 658-660.
    • (1994) J. Org. Chem. , vol.59 , pp. 658-660
    • Campbell, D.A.1    Bermak, J.C.2
  • 30
    • 0028134093 scopus 로고
    • Solid-phase synthesis of peptidylphosphonates
    • Campbell DA, Bermak JC. Solid-phase synthesis of peptidylphosphonates. J. Am. Chem. Soc. 1994; 116: 6039-6340.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6039-6340
    • Campbell, D.A.1    Bermak, J.C.2
  • 31
    • 0001700778 scopus 로고
    • Synthesis of phosphonic monoesters from phosphonous acids
    • Karanewsky DS, Badia MC. Synthesis of phosphonic monoesters from phosphonous acids. Tetrahedron Lett. 1986; 27: 1751-1754.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1751-1754
    • Karanewsky, D.S.1    Badia, M.C.2
  • 32
    • 0033803811 scopus 로고    scopus 로고
    • A facile synthesis of N-protected 1-aminoalkylphosphonamidate derivatives
    • Xu JX, Fu NY. A facile synthesis of N-protected 1-aminoalkylphosphonamidate derivatives. Synth. Commun. 2000; 30: 4137-4145.
    • (2000) Synth. Commun. , vol.30 , pp. 4137-4145
    • Xu, J.X.1    Fu, N.Y.2
  • 33
    • 0034920735 scopus 로고    scopus 로고
    • A novel and convenient method for synthesizing unsymmetrical N-benzyloxycarbonyl-protected 1-amino-l-aryl-alkylphosphonate mixed diesters
    • Xu JX, Fu NY. A novel and convenient method for synthesizing unsymmetrical N-benzyloxycarbonyl-protected 1-amino-l-aryl-alkylphosphonate mixed diesters. J. Chem. Soc., Perkin Trans. 1 2001; 1223-1226.
    • (2001) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1223-1226
    • Xu, J.X.1    Fu, N.Y.2
  • 34
    • 0034939111 scopus 로고    scopus 로고
    • A convenient method for the synthesis of N-protected 1-aminoalkyl-phosphonate mixed monothioesters and dithioesters
    • Xu JX, Wei M. A convenient method for the synthesis of N-protected 1-aminoalkyl-phosphonate mixed monothioesters and dithioesters. Synth. Commun. 2001; 31: 1489-1497.
    • (2001) Synth. Commun. , vol.31 , pp. 1489-1497
    • Xu, J.X.1    Wei, M.2
  • 35
    • 0027982561 scopus 로고
    • Peptide bond formation via catalytic antibodies: Synthesis of a novel phosphonate diester hapten
    • Smith AB III, Taylor CM, Benkovic SJ, Hirschmann R. Peptide bond formation via catalytic antibodies: synthesis of a novel phosphonate diester hapten. Tetrahedron Lett. 1994; 35: 6853-6856.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6853-6856
    • Smith III, A.B.1    Taylor, C.M.2    Benkovic, S.J.3    Hirschmann, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.