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Synthesis and glycosidase inhibitory activity of some N-Substituted 6-Deoxy-5a-carba-β-dl- and l-galactopyranosylamines

✍ Scribed by Seiichiro Ogawa; Shigeo Fujieda; Yuko Sakata; Masahiro Ishizaki; Seiichi Hisamatsu; Kensuke Okazaki

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 139 KB
Volume: 13
Category: Article
ISSN: 0960-894X
DOI: 10.1016/s0960-894x(03)00742-x

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✦ Synopsis

Chemical modification of 5a-carba-b-dl-fucopyranosylamine (3) generated six N-substituted derivatives 9a-f, among which N-octyl 9b, decyl 9c, and phenylbutyl ones 9f were found to be very strong b-galactosidase as well as b-glucosidase inhibitors. The inhibitory activity appeared attributable to d-enantiomers from biological assays of prepared l-enantiomers. Therefore, 6-deoxy-5a-carba-b-d-galactopyranosylamine (D-3) might be a promising lead compound for further design of new carba sugartype b-galactosidase inhibitors.

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