Flexible enantiodivergent synthesis and biological activity of mannostatin analogues, new cyclitol glycosidase inhibitors

被引：23
|
作者：
Nishimura, Y
Umezawa, Y
Adachi, H
Kondo, S
Takeuchi, T
机构：
[1] Institute of Microbial Chemistry, Shinagawa-ku, Tokyo 141
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期
关键词：
D O I：
10.1021/jo951126v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mannostatin A (1) is a new cyclitol inhibitor of glycoprotein processing. 2-Epimannostatin A (12) and its enantiomer (13) as well as their positional isomers (14, 15) were designed for probing structure-activity relationships in this class of glycosidase inhibitors. The analogues have been synthesized from (S)-4-((tert-butyldimethylsilyl)oxy)-2-cyclopentenone by an enantiodivergent strategy in a totally stereospecific fashion. Compound 13 showed inhibition against almond P-glucosidase and is shown to be a topographical analogue of beta-D-glucopyranoside.
引用
收藏
页码：480 / 488
页数：9
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