gem-Diamine 1-N-iminosugars of L-fucose-type, the extremely potent L-fucosidase inhibitors

被引：24

作者：

Shitara, E ^{[1
]}

Nishimura, Y ^{[1
]}

Kojima, F ^{[1
]}

Takeuchi, T ^{[1
]}

机构：

[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 02期

关键词：

gem-diamine; 1-N-iminosugar; L-fucosidase inhibitor; (2S,3S,4R,5R)-2-trifluoroacetamido-5-methylpiperidine-3,4-dial; cyclic methanediamine;

D O I：

10.1016/S0968-0896(99)00289-8

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：

An efficient route from D-ribono-gamma-lactone to gem-diamine 1-N-iminosugars of L-fucose-type, a new family of glycosidase inhibitor, has been developed in a formation of a gem-diamine 1-N-iminopyranose ring by the Mitsunobu reaction of an aminal as a key step. The analogues were proved to be the extremely potent inhibitors against alpha-L-fucosidase (IC50 similar to 3 ng mL(-1) K-i similar to 5x10(-9) M). The present study has shown that a cyclic methanediamine generated in media affects glycosidases as a real active-form of the gem-diamine 1-N-iminosugars of L-fucose-type. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：343 / 352

页数：10

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