THE SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF A PAIR OF DIASTEREOMERIC, CONFORMATIONALLY CONSTRAINED PEPTIDES WITH OPPOSITE AMIDE BOND GEOMETRIES

被引：16

作者：

CUMBERBATCH, S ^{[1
]}

NORTH, M ^{[1
]}

ZAGOTTO, G ^{[1
]}

机构：

[1] UNIV WALES,DEPT CHEM,BANGOR LL57 2UW,GWYNEDD,WALES

来源：

TETRAHEDRON | 1993年 / 49卷 / 40期

关键词：

D O I：

10.1016/S0040-4020(01)91222-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eight membered ring containing, conformationally constrained peptides derived from cyclo-[(R)-cysteinyl-(R)-penicillamine] contain a cis amide bond, whilst the diastereomeric peptides derived from cyclo-[(R)-cysteinyl-(S)-penicillamine] contain a trans amide bond.

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收藏

页码：9049 / 9066

页数：18

相关论文

共 26 条

[1] SOLID-STATE AND SOLUTION CONFORMATION OF PHENYLACETYL-L-CYSTEINYL-D-PENICILLAMINE CYCLIC DISULFIDE METHYL-ESTER - A CYCLIC DIPEPTIDE CONTAINING A TRANS AMIDE [J].

BAXTER, RL ;

GLOVER, SSB ;

GORDON, EM ;

GOULD, RO ;

MCKIE, MC ;

SCOTT, AI ;

WALKINSHAW, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02) :365-371

[2] APPROACHES TO PEPTIDOMIMETICS WHICH SERVE AS SURROGATES FOR THE CIS AMIDE BOND - NOVEL DISULFIDE-CONSTRAINED BICYCLIC HEXAPEPTIDE ANALOGS OF SOMATOSTATIN [J].

BRADY, SF ;

PALEVEDA, WJ ;

ARISON, BH ;

SAPERSTEIN, R ;

BRADY, EJ ;

RAYNOR, K ;

REISINE, T ;

VEBER, DF ;

FREIDINGER, RM .

TETRAHEDRON, 1993, 49 (17) :3449-3466

[3]

Bystrov V. F., 1973, Pure and Applied Chemistry, V36, P19, DOI 10.1351/pac197336010019

[4] STRUCTURE OF A CIS-PEPTIDE UNIT - MOLECULAR-CONFORMATION OF CYCLIC DISULFIDE L-CYSTEINYL-L-CYSTEINE [J].

CAPASSO, S ;

MATTIA, C ;

MAZZARELLA, L ;

PULITI, R .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (JUL15) :2080-2083

[5] CONFORMATIONAL-ANALYSIS OF THE CYCLIC DISULFIDE L-CYSTEINYL-L-CYSTEINE [J].

CAPASSO, S ;

MAZZARELLA, L ;

TANCREDI, T .

BIOPOLYMERS, 1979, 18 (06) :1555-1558

[6] STEREOCHEMICAL STUDIES OF CYCLIC PEPTIDES .4. ENERGY CALCULATIONS OF CYCLIC DISULPHIDE CYSTEINYLCYSTEINE [J].

CHANDRAS.R ;

BALASUBR.R .

BIOCHIMICA ET BIOPHYSICA ACTA, 1969, 188 (01) :1-&

[7]

CHANDRASEKHARAN R, 1968, Proceedings of the Indian Academy of Sciences Section A, V68, P13

[8] THE SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF A PAIR OF DIASTEREOISOMERIC CYCLIC-PEPTIDES WITH CIS AND TRANS AMIDE BONDS, RESPECTIVELY [J].

CUMBERBATCH, S ;

NORTH, M ;

ZAGOTTO, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (07) :641-642

[9]

FUJIMURA K, 1992, J CHEM RES-S, P88

[10] TERT-BUTYLOXYCARBONYL-L-CYSTEINYL-L-CYSTEINE DISULFIDE METHYL-ESTER [J].

HATA, Y ;

MATSUURA, Y ;

TANAKA, N ;

ASHIDA, T ;

KAKUDO, M .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (NOV) :3561-3564