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L,D-二肽聚集体的片状结构:(S)-苯甘氨酰-(R)-苯甘氨酸与酰胺的包合物

Sheet structure of an L,D-dipeptide aggregate: inclusion compounds of (S)-phenylglycyl-(R)-phenylglycine with amides.

作者信息

Akazome Motohiro, Senda Kyoko, Ogura Katsuyuki

机构信息

Department of Materials Technology, Faculty of Engineering, Chiba University, 1-33 Yayoicho, Inageku, Japan.

出版信息

J Org Chem. 2002 Dec 13;67(25):8885-9. doi: 10.1021/jo0204451.

DOI:10.1021/jo0204451
PMID:12467403
Abstract

A simple dipeptide, (S)-phenylglycyl-(R)-phenylglycine (S,R-1), formed inclusion compounds with a small amide such as formamide, acetamide, N,N-dimethylformamide (DMF), or N,N-dimethylacetamide. By single-crystal X-ray analysis, the inclusion compounds were shown to have a wavy layer structure. The molecules of S,R-1 are arranged in parallel via ionic pairing of the carboxyl and amino groups to construct the wavy layers. The guest molecules were accommodated in a channel cavity between the layers by means of hydrogen bonding with (+)NH(3) of S,R-1. The cavity is surrounded by the phenyl groups of S,R-1 that conformationally rotate so as to make the cavity size fit the guest amide.

摘要

一种简单的二肽,(S)-苯基甘氨酰-(R)-苯基甘氨酸(S,R-1),与甲酰胺、乙酰胺、N,N-二甲基甲酰胺(DMF)或N,N-二甲基乙酰胺等小分子酰胺形成包合物。通过单晶X射线分析表明,这些包合物具有波浪层结构。S,R-1分子通过羧基和氨基的离子配对平行排列,构建波浪层。客体分子通过与S,R-1的(+)NH(3)形成氢键而容纳在层间的通道腔内。该腔被S,R-1的苯基围绕,苯基发生构象旋转以使腔的大小适合客体酰胺。

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