Synthesis of heteroanalogues of disaccharides as potential inhibitors of the processing mannosidase Class I enzymes

被引：19

作者：

Johnston, BD

Pinto, BM ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

[2] Simon Fraser Univ, Prot Engn Network, Ctr Excellence, Burnaby, BC V5A 1S6, Canada

来源：

CARBOHYDRATE RESEARCH | 1998年 / 310卷 / 1-2期

关键词：

5-thio-alpha-D-mannopyranosyl trichloroacetimidate; thio sugars; disaccharides; heteroatom analogues; mannosidase inhibitors;

D O I：

10.1016/S0008-6215(98)00162-1

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：

Three disaccharide analogues of alpha-D -Man-(l-->2)-alpha-D-Man-OMe in which the ring and/or glycosidic oxygen atoms have been replaced by sulfur have been synthesized as potential inhibitors of Class I mannosidase enzymes. Glycosylation of appropriately protected methyl alpha-D-mannopyranosides, having free alcohol or thiol functional groups at the 2-position, with 2,3,4,6-tetra-O-acetyl-5-thio-alpha-D-mannopyranosyl trichloroacetitmidate was selective for the synthesis of cr-linked disaccharides in the case of the 2-alcohols, but yielded an alpha/beta mixture in the case of the 2-thiol glycosyl accepters. A disaccharide containing a single sulfur in the linkage was synthesized by nucleophilic substitution of the 2-triflate of a methyl alpha-D-glucopyranoside derivative by the thiolate anion of 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranose. Protecting groups were removed by standard methods to give the free heterosubstituted disaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：17 / 25

页数：9

共 22 条

[11] AMINO ALCOHOL AND AMINO SUGAR SYNTHESIS BY BENZOYLCARBAMATE CYCLIZATION [J].