Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks

被引：35

作者：

Melean, LG ^{[1
]}

Love, KR ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

CARBOHYDRATE RESEARCH | 2002年 / 337卷 / 21-23期

关键词：

glucosamines; glycosyl phosphates; automated solid-phase synthesis;

D O I：

10.1016/S0008-6215(02)00299-9

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：

Glucosamines are common components of many biologically important oligosaccharides. Reported is a systematic evaluation of glucosamine phosphates and trichloroacetimidates as glycosylating agents for the efficient construction of beta-(1 --> 6) glucosamine linkages. A set of differentially protected glucosamine donors incorporating a host of amine protecting groups, including 2-phthaloyl, benzyloxycarbonyl (Z), trichloroetheoxycarbonyl (Troc) and trichloroacetyl (TCA) protective groups. were prepared. Donors were initially evaluated for reactivity and protecting group compatibility in a solution-phase study with a model 6-hydroxyl galactose acceptor. Based on these results, glucosamine donor 10 was selected for the solution-phase synthesis of a beta-(1 --> 6)-glucosamine pentasaccharide. Finally, building block 10 proved well suited for use in the automated solid-phase synthesis of a repeating unit trisaccharide. An assessment of glucosamine phosphate donors as potential glycosylating agents for a variety of glucosamine linkages is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1893 / 1916

页数：24

共 18 条

[1] Solid-phase oligosaccharide synthesis: Preparation of complex structures using a novel linker and different glycosylating agents [J].