The synthesis of 16-mercaptohexadecanyl glycosides for biosensor applications

被引：26

作者：

Kitov, PI ^{[1
]}

Railton, C ^{[1
]}

Bundle, DR ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB, Canada

来源：

CARBOHYDRATE RESEARCH | 1998年 / 307卷 / 3-4期

关键词：

16-mercaptohexadecanyl glycosides; P-k trisaccharide; asialo GM(1); asialo GM(2); amperometric biosensors;

D O I：

10.1016/S0008-6215(98)00053-6

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 P-k trisaccharide and the central disaccharide element of asialo GM(1) activated as their trichloroacetimidates were each used to glycosylate 16-(p-toluensulfonyloxy)hexadecanol 1. Displacement of the tosyl group by thiocyanate followed by sodium borohydride reduction and saponification afforded oligosaccharide 16-mercaptohexadecanyl glycosides that were isolated as the corresponding disulfides 6 and 17 unless oxygen was rigorously excluded from the solvents used for work-up. Dithiothreitol reduction of disulfides and subsequent isolation under an inert atmosphere with degassed solvents gave the thiols 7 and 18. Chemisorption of omega-glycosyl alkanethiols and alkanethiols onto gold electrodes produces self-assembled monolayers that can act as amperometric biosensors for the detection of proteins that bind to the immobilized oligosaccharide epitope. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：361 / 369

页数：9

共 27 条

[1] FORMATION OF MONOLAYERS BY THE COADSORPTION OF THIOLS ON GOLD - VARIATION IN THE HEAD GROUP, TAIL GROUP, AND SOLVENT [J].