DESIGN AND SYNTHESIS OF A CIS-GLY-PRO, TYPE-VI TURN, DIPEPTIDE MIMETIC AND ITS USE IN FMOC-SOLID PHASE PEPTIDE-SYNTHESIS

被引：39

作者：

GRAMBERG, D ^{[1
]}

ROBINSON, JA ^{[1
]}

机构：

[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(00)75983-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Fmoc-protected bicyclic molecules 7 and 8 have been produced as cis-Gly-Pro peptide mimetics in nine synthetic steps starting from optically pure (R)-2-allylproline. Their use in solid-phase peptide synthesis has been demonstrated by their incorporation into analogues of cis-Gly(6)-Pro(7)-bradykinin.

引用

页码：861 / 864

页数：4

共 45 条

[1] SYNTHESIS OF 1,2-DISUBSTITUTED PYRROLES - A CIS PEPTIDE-BOND SURROGATE [J].

ABELL, AD ;

HOULT, DA ;

JAMIESON, EJ .

TETRAHEDRON LETTERS, 1992, 33 (39) :5831-5832

[2]

Atherton E, 1989, SOLID PHASE PEPTIDE

[3] OBSERVATION OF A CIS AMIDE ISOMER WITHIN A LINEAR PEPTIDE [J].

BAIRAKTARI, E ;

MIERKE, DF ;

MAMMI, S ;

PEGGION, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5383-5383

[4] DESIGN AND SYNTHESIS OF A CONFORMATIONAL ANALOG OF DEOXYBOUVARDIN [J].

BOGER, DL ;

MYERS, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5385-5390

[5] FOLDING KINETICS OF PHAGE-T4 THIOREDOXIN [J].

BORDEN, KLB ;

RICHARDS, FM .

BIOCHEMISTRY, 1990, 29 (12) :3071-3077

[6] TRYPTOPHAN-CONTAINING 1,5-TETRAZOLE DIPEPTIDE ANALOGS - SYNTHESIS OF TRP-PSI[CN4]NLE AS A CIS AMIDE BOND SURROGATE [J].

BOTEJU, LW ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1993, 34 (11) :1757-1760

[7] STRUCTURE DETERMINATION OF A TETRASACCHARIDE - TRANSIENT NUCLEAR OVERHAUSER EFFECTS IN THE ROTATING FRAME [J].

BOTHNERBY, AA ;

STEPHENS, RL ;

LEE, JM ;

WARREN, CD ;

JEANLOZ, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) :811-813

[8] HYPOTHESIS ABOUT THE FUNCTION OF MEMBRANE-BURIED PROLINE RESIDUES IN TRANSPORT PROTEINS [J].

BRANDL, CJ ;

DEBER, CM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (04) :917-921

[9] 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

[10] CONFORMATIONAL DIVERSITY OF BRADYKININ IN AQUEOUS-SOLUTION [J].

DENYS, L ;

BOTHNERBY, AA ;

FISHER, GH ;

RYAN, JW .

BIOCHEMISTRY, 1982, 21 (25) :6531-6536

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