Synthesis and conformational analysis of a type VIb β-turn mimetic based on an eight-membered lactam

被引：32

作者：

Derrer, S ^{[1
]}

Davies, JE ^{[1
]}

Holmes, AB ^{[1
]}

机构：

[1] Univ Cambridge, Cambridge Ctr Mol Recognit, Chem Lab, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 17期

关键词：

D O I：

10.1039/b003791p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As part of a programme evaluating medium-ring lactams as peptide conformational constraints the trans-disubstituted lactam dipeptide (3S,8R)-3-acetylamino-8-methoxycarbamoylazocan-2-one (3) was selected as a template to mimic the type VI beta-turn conformation of natural polypeptides. The enantioselective synthesis of the eight-membered lactam 3 is discussed. The X-ray crystal structure of the methyl ester precursor of 3 shows a classical type VIb beta-turn conformation. Extensive H-1 NMR spectroscopic studies of the dipeptide 3 in polar solvents provided evidence for a type VI beta-turn. The analysis shows an equilibrium of two folded conformations.

引用

页码：2957 / 2967

页数：11

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