메뉴 건너뛰기




Volumn 39, Issue 5, 2010, Pages 1265-1280

Synthesis of α-carboxyphosphinopeptides derived from norleucine

Author keywords

Norleucine; Phosphinate; Phosphinic pseudopeptides; Phosphinopeptides; Pseudopetides; Solid phase synthesis

Indexed keywords

(1 AMINOPENTYL)PHOSPHINIC ACID; [(1 AMINOPENTYL)(HYDROXY)PHOSPHORYL]ACETAMIDE; [(1 AMINOPENTYL)(HYDROXY)PHOSPHORYL]ACETIC ACID; [1 [(DIPHENYLMETHYL)AMINO]PENTYL]PHOSPHINIC ACID; [1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL]PHOSPHINIC ACID; [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](ADAMATYLOXY)PHOSPHORYL]ACETIC ACID; [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](HYDROXY)PHOSPHORYL]ACETAMIDE; [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](HYDROXY)PHOSPHORYL]ACETIC ACID; [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](METHOXY)PHOSPHORYL]ACETAMIDE; ALPHA CARBOXYPHOSPHINOPEPTIDE DERIVATIVE; BENZYL [1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL]PHOSPHINATE; BENZYL [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](BENZYLOXY)PHOSPHORYL]ACETATE; BENZYL HYDROGEN [1 (BENZYLOXYCARBONYLAMINO)PENTYL]PHOSPHONATE; BROMOACETIC ACID; DIPHENYLMETHYLAMINE HYPOPHOSPHITE; METHYL [(1 AMINOPENTYL)(HYDROXY)PHOSPHORYL]ACETATE; METHYL [1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL]PHOSPHINATE; METHYL [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](ADAMANTYLOXY)PHOSPHORYL]ACETATE; METHYL [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](BENZYLOXY)PHOSPHORYL]ACETATE; METHYL [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](HYDROXY)PHOSPHORYL]ACETATE; METHYL [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](METHOXY)PHOSPHORYL]ACETATE; METHYL HYDROGEN [1 (BENZYLOXYCARBONYLAMINO)PENTYL]PHOSPHONATE; NORLEUCINE; O METHYL S PHENYL [1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL]PHOSPHONOTHIATE; PHOSPHINIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; TERT BUTYL [[1 [[(BENZYLOXY)CARBONYL]AMINO]PENTYL](BENZYLOXY)PHOSPHORYL]ACETATE; UNCLASSIFIED DRUG;

EID: 78449282145     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0561-z     Document Type: Article
Times cited : (4)

References (50)
  • 1
    • 11444261600 scopus 로고
    • Acid-catalyzed hydrolysis of phosphinatesIII. The mechanism of hydrolysis of methyl and benzyl dialkylphosphinates
    • 1:CAS:528:DyaE1cXovVyqsQ%3D%3D 10.1139/v77-527
    • KA Abbas RD Cook 1977 Acid-catalyzed hydrolysis of phosphinatesIII. The mechanism of hydrolysis of methyl and benzyl dialkylphosphinates Can J Chem 55 3740 3750 1:CAS:528:DyaE1cXovVyqsQ%3D%3D 10.1139/v77-527
    • (1977) Can J Chem , vol.55 , pp. 3740-3750
    • Abbas, K.A.1    Cook, R.D.2
  • 2
    • 0024409372 scopus 로고
    • Renin inhibitors-synthesis of transition-state analog inhibitors containing phosphorus-acid derivatives at the scissile bond
    • 1:CAS:528:DyaL1MXksFygsLc%3D 10.1021/jm00127a041 2661820
    • MC Allen W Fuhrer B Tuck R Wade JM Wood 1989 Renin inhibitors-synthesis of transition-state analog inhibitors containing phosphorus-acid derivatives at the scissile bond J Med Chem 32 1652 1661 1:CAS:528:DyaL1MXksFygsLc%3D 10.1021/jm00127a041 2661820
    • (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
  • 3
    • 0028579715 scopus 로고
    • A structural comparison of 21-inhibitor complexes of the aspartic proteinase from Endothia parasitica
    • 1:CAS:528:DyaK2MXivFGms74%3D 10.1002/pro.5560031126 7703859
    • D Bailey JB Cooper 1994 A structural comparison of 21-inhibitor complexes of the aspartic proteinase from Endothia parasitica Protein Sci 3 2129 2143 1:CAS:528:DyaK2MXivFGms74%3D 10.1002/pro.5560031126 7703859
    • (1994) Protein Sci , vol.3 , pp. 2129-2143
    • Bailey, D.1    Cooper, J.B.2
  • 4
    • 33845470990 scopus 로고
    • Phosphinic acid dipeptide analogs-potent, slow-binding inhibitors of aspartic peptidases
    • 1:CAS:528:DyaL2cXksleju7o%3D 10.1021/ja00327a046
    • PA Bartlett WB Kezer 1984 Phosphinic acid dipeptide analogs-potent, slow-binding inhibitors of aspartic peptidases J Am Chem Soc 106 4282 4283 1:CAS:528:DyaL2cXksleju7o%3D 10.1021/ja00327a046
    • (1984) J Am Chem Soc , vol.106 , pp. 4282-4283
    • Bartlett, P.A.1    Kezer, W.B.2
  • 5
    • 0026083002 scopus 로고
    • Potent inhibition of pepsin and penicillopepsin by phosphorus-containing peptide analogs
    • 1:CAS:528:DyaK3MXntFyk 10.1021/jo00313a012
    • PA Bartlett JE Hanson PP Giannousis 1990 Potent inhibition of pepsin and penicillopepsin by phosphorus-containing peptide analogs J Org Chem 55 6268 6274 1:CAS:528:DyaK3MXntFyk 10.1021/jo00313a012
    • (1990) J Org Chem , vol.55 , pp. 6268-6274
    • Bartlett, P.A.1    Hanson, J.E.2    Giannousis, P.P.3
  • 6
    • 0013610276 scopus 로고
    • 1-Aminoalkylphosphonous acids. 1. Isosteres of the protein amino-acids
    • 10.1039/p19840002845
    • EK Baylis CD Campbell JG Dingwall 1984 1-Aminoalkylphosphonous acids. 1. Isosteres of the protein amino-acids J Chem Soc Perkin Trans 1 2845 2853 10.1039/p19840002845
    • (1984) J Chem Soc Perkin Trans , vol.1 , pp. 2845-2853
    • Baylis, E.K.1    Campbell, C.D.2    Dingwall, J.G.3
  • 7
    • 0010474508 scopus 로고
    • A theoretical-study of the active-site complexes formed between endothiapepsin and three potent inhibitors-pepstatin-A, and peptide analogs containing difluorostatone and phosphostatine-implications for inhibitor design
    • 1:CAS:528:DyaK2MXks1Kkurs%3D 10.1016/0166-1280(94)03937-G
    • AJ Beveridge C Dealwis JB Cooper 1995 A theoretical-study of the active-site complexes formed between endothiapepsin and three potent inhibitors-pepstatin-A, and peptide analogs containing difluorostatone and phosphostatine-implications for inhibitor design Theochem J Mol Struct 333 87 97 1:CAS:528:DyaK2MXks1Kkurs%3D 10.1016/0166-1280(94)03937-G
    • (1995) Theochem J Mol Struct , vol.333 , pp. 87-97
    • Beveridge, A.J.1    Dealwis, C.2    Cooper, J.B.3
  • 11
    • 0036311072 scopus 로고    scopus 로고
    • Five atomic resolution structures of endothiapepsin inhibitor complexes: Implications for the aspartic proteinase mechanism
    • 1:CAS:528:DC%2BD38Xkslykt7w%3D 10.1016/S0022-2836(02)00197-3 12083527
    • L Coates PT Erskine MP Crump SP Wood JB Cooper 2002 Five atomic resolution structures of endothiapepsin inhibitor complexes: implications for the aspartic proteinase mechanism J Mol Biol 318 1405 1415 1:CAS:528: DC%2BD38Xkslykt7w%3D 10.1016/S0022-2836(02)00197-3 12083527
    • (2002) J Mol Biol , vol.318 , pp. 1405-1415
    • Coates, L.1    Erskine, P.T.2    Crump, M.P.3    Wood, S.P.4    Cooper, J.B.5
  • 12
    • 0034042865 scopus 로고    scopus 로고
    • Phosphinic acid compounds in biochemistry, biology and medicine
    • 1:CAS:528:DC%2BD3cXjtlKjsr4%3D 10702630
    • M Collinsova J Jiracek 2000 Phosphinic acid compounds in biochemistry, biology and medicine Curr Med Chem 7 629 647 1:CAS:528:DC%2BD3cXjtlKjsr4%3D 10702630
    • (2000) Curr Med Chem , vol.7 , pp. 629-647
    • Collinsova, M.1    Jiracek, J.2
  • 13
    • 0037330285 scopus 로고    scopus 로고
    • Combining combinatorial chemistry and affinity chromatography: Highly selective inhibitors of human betaine: Homocysteine S-methyltransferase
    • 1:CAS:528:DC%2BD3sXhs1Crsrw%3D 10.1016/S1074-5521(03)00008-5 12618183
    • M Collinsova C Castro TA Garrow A Yiotakis V Dive J Jiracek 2003 Combining combinatorial chemistry and affinity chromatography: highly selective inhibitors of human betaine: homocysteine S-methyltransferase Chem Biol 10 113 122 1:CAS:528:DC%2BD3sXhs1Crsrw%3D 10.1016/S1074-5521(03)00008-5 12618183
    • (2003) Chem Biol , vol.10 , pp. 113-122
    • Collinsova, M.1    Castro, C.2    Garrow, T.A.3    Yiotakis, A.4    Dive, V.5    Jiracek, J.6
  • 15
    • 13044297058 scopus 로고    scopus 로고
    • RXP 407, a phosphinic peptide, is a potent inhibitor of angiotensin i converting enzyme able to differentiate between its two active sites
    • 1:CAS:528:DyaK1MXjs1ymu70%3D 10.1073/pnas.96.8.4330 10200262
    • V Dive J Cotton A Yiotakis A Michaud S Vassiliou J Jiracek G Vazeux MT Chauvet P Cuniasse P Corvol 1999 RXP 407, a phosphinic peptide, is a potent inhibitor of angiotensin I converting enzyme able to differentiate between its two active sites Proc Natl Acad Sci USA 96 4330 4335 1:CAS:528: DyaK1MXjs1ymu70%3D 10.1073/pnas.96.8.4330 10200262
    • (1999) Proc Natl Acad Sci USA , vol.96 , pp. 4330-4335
    • Dive, V.1    Cotton, J.2    Yiotakis, A.3    Michaud, A.4    Vassiliou, S.5    Jiracek, J.6    Vazeux, G.7    Chauvet, M.T.8    Cuniasse, P.9    Corvol, P.10
  • 16
    • 4344573848 scopus 로고    scopus 로고
    • Phosphinic peptides as zinc metalloproteinase inhibitors
    • 1:CAS:528:DC%2BD2cXotVyjsLY%3D 10.1007/s00018-004-4050-y 15316651
    • V Dive D Georgiadis M Matziari A Makaritis F Beau P Cuniasse A Yiotakis 2004 Phosphinic peptides as zinc metalloproteinase inhibitors Cell Mol Life Sci 61 2010 2019 1:CAS:528:DC%2BD2cXotVyjsLY%3D 10.1007/s00018-004-4050-y 15316651
    • (2004) Cell Mol Life Sci , vol.61 , pp. 2010-2019
    • Dive, V.1    Georgiadis, D.2    Matziari, M.3    Makaritis, A.4    Beau, F.5    Cuniasse, P.6    Yiotakis, A.7
  • 18
    • 0026619118 scopus 로고
    • A convenient synthetic approach to new alpha-(9- fluorenylmethoxycarbonylamino)alkylphosphonic acid-derivatives
    • Dumy P, Escale R, Girard JP, Parello J, Vidal JP (1992) A convenient synthetic approach to new alpha-(9-fluorenylmethoxycarbonylamino)alkylphosphonic acid-derivatives. Synthesis, pp 1226-1228
    • (1992) Synthesis , pp. 1226-1228
    • Dumy, P.1    Escale, R.2    Girard, J.P.3    Parello, J.4    Vidal, J.P.5
  • 19
    • 0025232814 scopus 로고
    • Solid-phase peptide-synthesis utilizing 9-fluorenylmethoxycarbonyl amino-acids
    • 1:CAS:528:DyaK3cXksVWhsbg%3D 10.1111/j.1399-3011.1990.tb00939.x
    • GB Fields RL Noble 1990 Solid-phase peptide-synthesis utilizing 9-fluorenylmethoxycarbonyl amino-acids Int J Pept Prot Res 35 161 214 1:CAS:528:DyaK3cXksVWhsbg%3D 10.1111/j.1399-3011.1990.tb00939.x
    • (1990) Int J Pept Prot Res , vol.35 , pp. 161-214
    • Fields, G.B.1    Noble, R.L.2
  • 20
    • 0002384506 scopus 로고
    • Synthesis of hypophosphite esters from orthocarbonyl compounds
    • 1:CAS:528:DyaF2cXit12htw%3D%3D 10.1021/ja01055a015
    • SJ Fitch 1964 Synthesis of hypophosphite esters from orthocarbonyl compounds J Am Chem Soc 86 61 64 1:CAS:528:DyaF2cXit12htw%3D%3D 10.1021/ja01055a015
    • (1964) J Am Chem Soc , vol.86 , pp. 61-64
    • Fitch, S.J.1
  • 21
    • 0026770573 scopus 로고
    • Crystallographic analysis of transition-state mimics bound to penicillopepsin-phosphorus-containing peptide analogs
    • 1:CAS:528:DyaK38XktVehsrg%3D 10.1021/bi00137a016 1606144
    • ME Fraser NCJ Strynadka PA Bartlett JE Hanson MNG James 1992 Crystallographic analysis of transition-state mimics bound to penicillopepsin-phosphorus-containing peptide analogs Biochemistry 31 5201 5214 1:CAS:528:DyaK38XktVehsrg%3D 10.1021/bi00137a016 1606144
    • (1992) Biochemistry , vol.31 , pp. 5201-5214
    • Fraser, M.E.1    Strynadka, N.C.J.2    Bartlett, P.A.3    Hanson, J.E.4    James, M.N.G.5
  • 22
    • 0035812676 scopus 로고    scopus 로고
    • Synthesis and comparative study on the reactivity of peptidyl-type phosphinic esters: Intramolecular effects in the alkaline and acidic cleavage of methyl beta-carboxyphosphinates
    • 1:CAS:528:DC%2BD3MXmsVyrtrs%3D 10.1021/jo0156363 11578210
    • D Georgiadis V Dive A Yiotakis 2001 Synthesis and comparative study on the reactivity of peptidyl-type phosphinic esters: intramolecular effects in the alkaline and acidic cleavage of methyl beta-carboxyphosphinates J Org Chem 66 6604 6610 1:CAS:528:DC%2BD3MXmsVyrtrs%3D 10.1021/jo0156363 11578210
    • (2001) J Org Chem , vol.66 , pp. 6604-6610
    • Georgiadis, D.1    Dive, V.2    Yiotakis, A.3
  • 23
    • 0035897135 scopus 로고    scopus 로고
    • A highly efficient method for the preparation of phosphinic pseudodipeptidic blocks suitably protected for solid-phase peptide synthesis
    • 1:CAS:528:DC%2BD3MXisl2htr8%3D 10.1016/S0040-4020(01)00221-6
    • D Georgiadis M Matziari A Yiotakis 2001 A highly efficient method for the preparation of phosphinic pseudodipeptidic blocks suitably protected for solid-phase peptide synthesis Tetrahedron 57 3471 3478 1:CAS:528: DC%2BD3MXisl2htr8%3D 10.1016/S0040-4020(01)00221-6
    • (2001) Tetrahedron , vol.57 , pp. 3471-3478
    • Georgiadis, D.1    Matziari, M.2    Yiotakis, A.3
  • 25
    • 0029155961 scopus 로고
    • Development of highly potent and selective phosphinic peptide inhibitors of zinc endopeptidase-24-15 using combinatorial chemistry
    • 1:CAS:528:DyaK2MXotFaisrc%3D 10.1074/jbc.270.37.21701 7665587
    • J Jiracek A Yiotakis B Vincent A Lecoq A Nicolaou F Checler V Dive 1995 Development of highly potent and selective phosphinic peptide inhibitors of zinc endopeptidase-24-15 using combinatorial chemistry J Biol Chem 270 21701 21706 1:CAS:528:DyaK2MXotFaisrc%3D 10.1074/jbc.270.37.21701 7665587
    • (1995) J Biol Chem , vol.270 , pp. 21701-21706
    • Jiracek, J.1    Yiotakis, A.2    Vincent, B.3    Lecoq, A.4    Nicolaou, A.5    Checler, F.6    Dive, V.7
  • 26
    • 0029741201 scopus 로고    scopus 로고
    • Development of the first potent and selective inhibitor of the zinc endopeptidase neurolysin using a systematic approach based on combinatorial chemistry of phosphinic peptides
    • 1:CAS:528:DyaK28XkvFymur0%3D 10.1074/jbc.271.32.19606 8702656
    • J Jiracek A Yiotakis B Vincent F Checler V Dive 1996 Development of the first potent and selective inhibitor of the zinc endopeptidase neurolysin using a systematic approach based on combinatorial chemistry of phosphinic peptides J Biol Chem 271 19606 19611 1:CAS:528:DyaK28XkvFymur0%3D 10.1074/jbc.271.32.19606 8702656
    • (1996) J Biol Chem , vol.271 , pp. 19606-19611
    • Jiracek, J.1    Yiotakis, A.2    Vincent, B.3    Checler, F.4    Dive, V.5
  • 29
    • 0342450035 scopus 로고
    • Synthesis of N-phosphorylated derivatives of amino acids
    • 1:CAS:528:DyaG28Xht1Skuw%3D%3D 10.1021/ja01612a048
    • SO Li RE Eakin 1955 Synthesis of N-phosphorylated derivatives of amino acids J Am Chem Soc 77 1866 1870 1:CAS:528:DyaG28Xht1Skuw%3D%3D 10.1021/ja01612a048
    • (1955) J Am Chem Soc , vol.77 , pp. 1866-1870
    • Li, S.O.1    Eakin, R.E.2
  • 30
    • 49149115268 scopus 로고    scopus 로고
    • Synthesis of methionine- and norleucine-derived phosphinopeptides
    • 1:CAS:528:DC%2BD1cXhtVWks7nK 10.1016/j.tetlet.2008.07.062
    • R Liboska J Picha I Hanclova M Budesinsky M Sanda J Jiracek 2008 Synthesis of methionine- and norleucine-derived phosphinopeptides Tetrahedron Lett 49 5629 5631 1:CAS:528:DC%2BD1cXhtVWks7nK 10.1016/j.tetlet.2008.07.062
    • (2008) Tetrahedron Lett , vol.49 , pp. 5629-5631
    • Liboska, R.1    Picha, J.2    Hanclova, I.3    Budesinsky, M.4    Sanda, M.5    Jiracek, J.6
  • 32
    • 0028578656 scopus 로고
    • The chemistry of phosphapeptides-investigations on the synthesis of phosphonamidate, phosphonate, and phosphinate analogs of glutamyl-gamma- glutamate
    • 1:CAS:528:DyaK2MXitFOgtro%3D 10.1021/jo00104a017
    • WP Malachowski JK Coward 1994 The chemistry of phosphapeptides- investigations on the synthesis of phosphonamidate, phosphonate, and phosphinate analogs of glutamyl-gamma-glutamate J Org Chem 59 7625 7634 1:CAS:528:DyaK2MXitFOgtro%3D 10.1021/jo00104a017
    • (1994) J Org Chem , vol.59 , pp. 7625-7634
    • Malachowski, W.P.1    Coward, J.K.2
  • 35
    • 30944449006 scopus 로고    scopus 로고
    • Synthesis of imidazole phosphinic acids as I4AA analogues
    • 1:CAS:528:DC%2BD28XotFKjtQ%3D%3D 10.1016/j.tetlet.2005.12.086
    • D Orain H Mattes 2006 Synthesis of imidazole phosphinic acids as I4AA analogues Tetrahedron Lett 47 1253 1255 1:CAS:528:DC%2BD28XotFKjtQ%3D%3D 10.1016/j.tetlet.2005.12.086
    • (2006) Tetrahedron Lett , vol.47 , pp. 1253-1255
    • Orain, D.1    Mattes, H.2
  • 39
    • 0026581791 scopus 로고
    • Transition-state characterization-a new approach combining inhibitor analogs and variation in enzyme structure
    • 1:CAS:528:DyaK38XnvFWgtQ%3D%3D 10.1021/bi00119a003 1734971
    • MA Phillips AP Kaplan WJ Rutter PA Bartlett 1992 Transition-state characterization-a new approach combining inhibitor analogs and variation in enzyme structure Biochemistry 31 959 963 1:CAS:528:DyaK38XnvFWgtQ%3D%3D 10.1021/bi00119a003 1734971
    • (1992) Biochemistry , vol.31 , pp. 959-963
    • Phillips, M.A.1    Kaplan, A.P.2    Rutter, W.J.3    Bartlett, P.A.4
  • 40
    • 44649185557 scopus 로고    scopus 로고
    • Synthesis of norleucine-derived phosphonopeptides
    • 1:CAS:528:DC%2BD1cXmvVyms7o%3D 10.1016/j.tetlet.2008.05.028
    • J Picha M Budesinsky M Sanda J Jiracek 2008 Synthesis of norleucine-derived phosphonopeptides Tetrahedron Lett 49 4366 4368 1:CAS:528:DC%2BD1cXmvVyms7o%3D 10.1016/j.tetlet.2008.05.028
    • (2008) Tetrahedron Lett , vol.49 , pp. 4366-4368
    • Picha, J.1    Budesinsky, M.2    Sanda, M.3    Jiracek, J.4
  • 41
    • 67649365619 scopus 로고    scopus 로고
    • Efficient synthesis of phos phonodepsipeptides derived from norleucine
    • 1:CAS:528:DC%2BD1MXotFCksbk%3D 10.1016/j.tet.2009.05.051
    • J Picha M Budesinsky I Hanclova M Sanda P Fiedler V Vanek J Jiracek 2009 Efficient synthesis of phos phonodepsipeptides derived from norleucine Tetrahedron 65 6090 6103 1:CAS:528:DC%2BD1MXotFCksbk%3D 10.1016/j.tet.2009.05. 051
    • (2009) Tetrahedron , vol.65 , pp. 6090-6103
    • Picha, J.1    Budesinsky, M.2    Hanclova, I.3    Sanda, M.4    Fiedler, P.5    Vanek, V.6    Jiracek, J.7
  • 43
    • 33845278913 scopus 로고
    • Synthesis of phosphonic acid-derivatives by oxidative activation of phosphinate esters
    • 1:CAS:528:DyaL1cXlt12lur4%3D 10.1021/jo00254a015
    • NS Sampson PA Bartlett 1988 Synthesis of phosphonic acid-derivatives by oxidative activation of phosphinate esters J Org Chem 53 4500 4503 1:CAS:528:DyaL1cXlt12lur4%3D 10.1021/jo00254a015
    • (1988) J Org Chem , vol.53 , pp. 4500-4503
    • Sampson, N.S.1    Bartlett, P.A.2
  • 44
    • 0028287938 scopus 로고
    • Transition state analysis and inhibitor design for enzymatic reactions
    • 1:CAS:528:DyaK2cXltVamtb8%3D 8034566
    • VL Schramm BA Horenstein PC Kline 1994 Transition state analysis and inhibitor design for enzymatic reactions J Biol Chem 269 18259 18262 1:CAS:528:DyaK2cXltVamtb8%3D 8034566
    • (1994) J Biol Chem , vol.269 , pp. 18259-18262
    • Schramm, V.L.1    Horenstein, B.A.2    Kline, P.C.3
  • 46
    • 0021128805 scopus 로고
    • Mild arbuzov reactions of phosphonous acids
    • 1:CAS:528:DyaL2MXhsV2gt70%3D 10.1016/S0040-4039(01)81506-9
    • JK Thottathil CA Przybyla JL Moniot 1984 Mild arbuzov reactions of phosphonous acids Tetrahedron Lett 25 4737 4740 1:CAS:528:DyaL2MXhsV2gt70%3D 10.1016/S0040-4039(01)81506-9
    • (1984) Tetrahedron Lett , vol.25 , pp. 4737-4740
    • Thottathil, J.K.1    Przybyla, C.A.2    Moniot, J.L.3
  • 47
    • 33644557736 scopus 로고    scopus 로고
    • Binding of phosphinate and phosphonate inhibitors to aspartic proteases: A first-principles study
    • 1:CAS:528:DC%2BD2MXhtlClsbbE 10.1021/jp0544639 16471695
    • P Vidossich P Carloni 2006 Binding of phosphinate and phosphonate inhibitors to aspartic proteases: a first-principles study J Phys Chem B 110 1437 1442 1:CAS:528:DC%2BD2MXhtlClsbbE 10.1021/jp0544639 16471695
    • (2006) J Phys Chem B , vol.110 , pp. 1437-1442
    • Vidossich, P.1    Carloni, P.2
  • 48
    • 0000631346 scopus 로고
    • Transition-state analogues
    • 1:CAS:528:DyaK38XhslCrug%3D%3D 10.1016/0959-440X(91)90179-W
    • R Wolfenden A Radzicka 1991 Transition-state analogues Curr Opin Struct Biol 1 780 787 1:CAS:528:DyaK38XhslCrug%3D%3D 10.1016/0959-440X(91)90179-W
    • (1991) Curr Opin Struct Biol , vol.1 , pp. 780-787
    • Wolfenden, R.1    Radzicka, A.2
  • 49
    • 0029821713 scopus 로고    scopus 로고
    • Protection of the hydroxyphosphinyl function of phosphinic dipeptides by adamantyl Application to the solid-phase synthesis of phosphinic peptides
    • 1:CAS:528:DyaK28XltlWkt70%3D 10.1021/jo9603439 11667528
    • A Yiotakis S Vassiliou J Jiracek V Dive 1996 Protection of the hydroxyphosphinyl function of phosphinic dipeptides by adamantyl Application to the solid-phase synthesis of phosphinic peptides J Org Chem 61 6601 6605 1:CAS:528:DyaK28XltlWkt70%3D 10.1021/jo9603439 11667528
    • (1996) J Org Chem , vol.61 , pp. 6601-6605
    • Yiotakis, A.1    Vassiliou, S.2    Jiracek, J.3    Dive, V.4
  • 50
    • 3242767802 scopus 로고    scopus 로고
    • Phosphinic peptides: Synthetic approaches and biochemical evaluation as Zn-metalloprotease inhibitors
    • 1:CAS:528:DC%2BD2cXlslWmurg%3D 10.2174/1385272043370177
    • A Yiotakis D Georgiadis M Matziari A Makaritis V Dive 2004 Phosphinic peptides: synthetic approaches and biochemical evaluation as Zn-metalloprotease inhibitors Curr Org Chem 8 1135 1158 1:CAS:528:DC%2BD2cXlslWmurg%3D 10.2174/1385272043370177
    • (2004) Curr Org Chem , vol.8 , pp. 1135-1158
    • Yiotakis, A.1    Georgiadis, D.2    Matziari, M.3    Makaritis, A.4    Dive, V.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.