Syntheses of chondroitin 4-and 6-sulfate pentasaccharide derivatives having a methyl β-D-glucopyranosiduronic acid at the reducing end

被引:25
作者
Bélot, F [1 ]
Jacquinet, JC [1 ]
机构
[1] Univ Orleans, CNRS, UFR Fac Sci, UPRES A 6005,Inst Chim Organ & Analyt, F-45067 Orleans, France
关键词
pentasaccharide; chondroitin; 4; and; 6-sulfate; glycosaminoglycans;
D O I
10.1016/S0008-6215(00)00032-X
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The syntheses are reported of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpA-(1 --> OMe), O-sulfonated at C-4 or C-6 of the aminosugar moieties, which represent structural elements of chondroitin 4- and 6-sulfate proteoglycans. Starting from a synthetic disaccharide glycosyl acceptor, the stepwise or blockwise construction of the sugar backbone with appropriate synthons led to a pentasaccharide tetraol, which was used as a common intermediate. Selective 6-O-sulfonation of this tetraol, followed by saponification, gave the 6-sulfate derivative, whereas selective 6-O-benzoylation, followed by O-sulfonation and saponification, afforded the 4-sulfate derivative as their sodium salts. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:88 / 97
页数:10
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