Influence of cis-trans isomerisation on pentapeptide cyclisation

被引：13
作者：
Sager, C [1 ]
Mutter, M [1 ]
Dumy, P [1 ]
机构：
[1] Univ Lausanne, Inst Organ Chem, Lausanne, Switzerland
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 45期
关键词：
peptide cyclisation; cis-trans isomerisation; conformation;
D O I：
10.1016/S0040-4039(99)01671-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclisation reactions on pentapeptides containing the turn promoting residues Gly and Pro are investigated. Although the cyclisation reaction is fast, solvent-dependent mixtures of cyclic penta- and decapeptides are observed. NMR studies suggest a strong dependence of the monomer/dimer ratio on the cis-trans isomerisation found in linear and cyclic peptides. The critical influence on ring closure of a cis Xaa-Pro peptide bond conformation is demonstrated by using the cis peptide bond-inducing residue 2,2-dimethyl-1,3-thiazolidine-4 carboxylic acid (Dmt, pseudo-proline) as proline substitute. The results shed new light on the role of cis-trans isomerisation in pentapeptide cyclisation. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7987 / 7991
页数：5
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