New derivatives of reducing oligosaccharides and their use in enzymatic reactions:: efficient synthesis of sialyl Lewis a and sialyl dimeric Lewis x glycoconjugates

被引：21

作者：

Bårström, M ^{[1
]}

Bengtsson, M ^{[1
]}

Blixt, O ^{[1
]}

Norberg, T ^{[1
]}

机构：

[1] Swedish Univ Agr Sci, Dept Chem, S-75007 Uppsala, Sweden

来源：

CARBOHYDRATE RESEARCH | 2000年 / 328卷 / 04期

关键词：

derivatives; oligosaccharides; enzymatic reactions;

D O I：

10.1016/S0008-6215(00)00128-2

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 reducing oligosaccharides lactose and lacto-N-tetraose were reductively aminated with benzyloxycarbonylaminoaniline and sodium cyanoborohydride, followed by treatment of the resulting secondary amines with acetic anhydride. The resulting N-acetyl-N-(4-benzyroxycarbonylaminophenyl)-1-amino-1-deoxyalditol oligosaccharide derivatives were subjected to stepwise enzymatic elongation with various glycosyltransferases/nucleotide sugars. Purification of the products after each enzymatic step was conveniently performed by solid-phase extraction on silica gel C-ls cartridges. Two oligosaccharide derivatives (with sialyl Lewis a and sialyl dimeric Lewis x structures) were prepared. Conversion of the obtained derivatives into neoglycoproteins by the sequence hydrogenolysis, thiophosgene treatment, and protein coupling was carried out. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：525 / 531

页数：7

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