Anomer-selective inhibition of glycosidases using aminocyclopentanols

Authors
Leroy, E Raymond, JL
Citation
E. Leroy et Jl. Raymond, Anomer-selective inhibition of glycosidases using aminocyclopentanols, ORG LETT, 1(5), 1999, pp. 775-777
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
5
Year of publication
1999
Pages
775 - 777
Database
ISI
SICI code
1523-7060(19990909)1:5<775:AIOGUA>2.0.ZU;2-W
Abstract
[GRAPHICS] (1S,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1 is pre pared stereoselectively from D-lyxose and displays anomer selective inhibit ion for beta galactosidase (K-i = 3.0 x 10(-6) M) and beta-glucosidase (K-i = 1.5 x 10(-7) M), over alpha-galactosidase (K-i = 2.3 x 10(-5) M) and a g lucosidase (IC50 = 1.0 x 10(-4) M), There is no observable cross-reactivity with alpha-mannosidase, beta-mannosidase, or alpha-L-fucosidase.