Stereoselective inhibition of alpha-L-fucosidases by N-benzyl aminocyclopentitols

Authors
Blaser, A Reymond, JL
Citation
A. Blaser et Jl. Reymond, Stereoselective inhibition of alpha-L-fucosidases by N-benzyl aminocyclopentitols, ORG LETT, 2(12), 2000, pp. 1733-1736
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
12
Year of publication
2000
Pages
1733 - 1736
Database
ISI
SICI code
1523-7060(20000615)2:12<1733:SIOABN>2.0.ZU;2-R
Abstract
[GRAPHICS] (1R,2R,3R,4R,5R)-4-Amino-5-methylcyclopentane-1,2,3-triol 8, its 4S stereoi somer 9, and their acyclic analogues (R)- and (S)-5-aminobutanol 11 and 12 are selective but moderate inhibitors of alpha-L-fucosidases. N-Benzylation selectively enhances inhibition potency for aminocyclopentitol 8 ( --> 1, K-i = 6.8 x 10(-7) M) but decreases inhibition for its 4S-stereoisomer 9 (- -> 2, K-i = 1.1 x 10(-4) M) and for the aminobutanols 11 ( --> 13, no inhib ition) and 12 ( --> 14, no inhibition).