STEREOSELECTIVE SYNTHESIS OF O-SERINYL/THREONINYL-2-ACETAMIDO-2-DEOXY-ALPHA-GLYCOSIDES OR O-SERINYL/THREONINYL-2-ACETAMIDO-2-DEOXY-BETA-GLYCOSIDES

被引：28

作者：

SZABO, L ^{[1
]}

RAMZA, J ^{[1
]}

LANGDON, C ^{[1
]}

POLT, R ^{[1
]}

机构：

[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721

来源：

CARBOHYDRATE RESEARCH | 1995年 / 274卷

基金：

美国国家科学基金会;

关键词：

2-ACETAMIDO-2-DEOXY-GLYCOSIDES; STEREOSELECTIVE SYNTHESIS;

D O I：

10.1016/0008-6215(95)00016-M

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：

General glycosidation methodology has been developed which can selectively provide 2acetamido-2-deoxy-alpha- or beta-glycosides of beta-hydroxy-alpha-amino acid derivatives [glucopyranoside- (8, 43), galactopyranoside- (9, 13), mannopyranoside- (10), lactoside analogs (11, 38) and 3-O-beta-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic a-imino esters (Schiff bases) of L-serine and L-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl- or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete H-1- and C-13-NMR data are provided for all compounds.

引用

页码：11 / 28

页数：18

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