Pseudosugars, 41 - Synthesis and glycosidase inhibitory activity of 5a-carba-alpha-DL-fucopyranosylamine and -galactopyranosylamine

Authors
Ogawa, S Sekura, R Maruyama, A Yuasa, H Hashimoto, H
Citation
S. Ogawa et al., Pseudosugars, 41 - Synthesis and glycosidase inhibitory activity of 5a-carba-alpha-DL-fucopyranosylamine and -galactopyranosylamine, EUR J ORG C, (11), 2000, pp. 2089-2093
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
2000
Pages
2089 - 2093
Database
ISI
SICI code
1434-193X(200006):11<2089:P4-SAG>2.0.ZU;2-#
Abstract
5a-Carba-alpha-DL-fucopyranosylamine (DL-5) and -galactopyranosylamine (DL- 4) have been synthesized in a conventional manner from 2,3,4,6-tetra-O-acet yl-5a-carba-beta-DL-glucpyranosyl bromide (6), Only compound DL-5 has been shown to be a strong inhibitor (K-i = 2.3 X 10(-7) m) of alpha-fucosidase ( bovine kidney). They did not exhibit any inhibitory activity towards five g lycoside hydrolases, namely alpha- and beta-glucosidases and alpha- and bet a-galactosidases.