Synthesis and conformational analysis of a dimerising eight-membered lactam dipeptide

被引：14

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/b003789n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The eight-membered lactam dipeptide (3R,8R)-3-acetylamino-8-methoxycarbamoylazocan-2-one was prepared from the L-serine derived (4S)-3-tert-butyloxycarbonyl-4-formyl-2,2-dimethyl-1,3-oxazolidine in 12 steps and 27% overall yield. An extensive conformational analysis both in the solid state and in solution, using NMR, IR and vapour pressure osmometry, was conducted. It was shown that the constrained dipeptide exists in a semi-extended conformation and exhibits a head-to-tail self-recognition (K-dim 100+/-20 dm(3) mol(-1) in CDCl2CDCl2). This dimerisation appears to be a general phenomenon in a series of cis-disubstituted medium-ring lactam dipeptides.

引用

页码：2943 / 2956

页数：14

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