几种哺乳动物蛋白聚糖共有的碳水化合物-蛋白质连接区域的全合成。

Total synthesis of the carbohydrate-protein linkage region common to several mammalian proteoglycans.

作者信息

Rio S, Beau J M, Jacquinet J C

机构信息

Laboratoire de Biochimie Structurale, U.R.A. 499, U.F.R. Faculté des Sciences, Université d'Orléans, France.

出版信息

Carbohydr Res. 1993 Jun 21;244(2):295-313. doi: 10.1016/0008-6215(83)85009-5.

DOI:10.1016/0008-6215(83)85009-5

PMID:8348554

Abstract

A stereocontrolled synthesis of beta-D-GlcpA-(1--> 3)-beta-D-Galp-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Xylp-(1 --> O)-L-Ser-Gly, the common glycopeptide sequence of the carbohydrate-protein linkage region of most mammalian proteoglycans, was achieved by use of O-[2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-beta-D-glucopyranosyluronate] -(1-->3)-O-(2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl)-(1-->3)-O-(2,4, 6-tri -O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-2,3-di-O-benzoyl-alpha, beta-D- xylopyranosyl trichloroacetimidate as the key intermediate. Condensation of this glycosyl donor with suitably protected L-seryl-glycine dipeptide segments, and peptide chain elongation, allowed the construction in high yield of complex structures of this linkage region.

摘要

通过使用O-[2-(三甲基甲硅烷基)乙基2,3,4-三-O-苯甲酰基-β-D-吡喃葡萄糖醛酸酯]-(1→3)-O-(2,4,6-三-O-苯甲酰基-β-D-吡喃半乳糖基)-(1→3)-O-(2,4,6-三-O-苯甲酰基-β-D-吡喃半乳糖基)-(1→4)-2,3-二-O-苯甲酰基-α,β-D-吡喃木糖基三氯乙酰胺作为关键中间体，实现了β-D-葡萄糖醛酸-(1→3)-β-D-半乳糖-(1→3)-β-D-半乳糖-(1→4)-β-D-木糖-(1→O)-L-丝氨酸-甘氨酸的立体控制合成，这是大多数哺乳动物蛋白聚糖碳水化合物-蛋白质连接区常见的糖肽序列。该糖基供体与适当保护的L-丝氨酰-甘氨酸二肽片段的缩合以及肽链的延长，使得能够高产率地构建该连接区的复杂结构。