Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

被引:50
作者
Andersen, SM
Ekhart, C
Lundt, I
Stütz, AE
机构
[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark
[2] Graz Tech Univ, Inst Organ Chem, A-8010 Graz, Austria
关键词
trihydroxy azepanes; glycosidase inhibitors; simple carbohydrates;
D O I
10.1016/S0008-6215(00)00018-5
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
Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-l,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-riho-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:22 / 33
页数:12
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