Synthesis and evaluation of aminocyclopentitol inhibitors of beta-glucosidases

Authors
Boss, O Leroy, E Blaser, A Reymond, JL
Citation
O. Boss et al., Synthesis and evaluation of aminocyclopentitol inhibitors of beta-glucosidases, ORG LETT, 2(2), 2000, pp. 151-154
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
2
Year of publication
2000
Pages
151 - 154
Database
ISI
SICI code
1523-7060(20000127)2:2<151:SAEOAI>2.0.ZU;2-A
Abstract
[GRAPHICS] (1R,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1, prepa red from D-glucose, inhibits beta-glucosidases from Caldocellum saccharolyt icum (K-i = 1.8 x 10(-7) M) and from almonds (K-i = 3.4 x 10(-6) M). Inhibi tion is not influenced by N-ethylation (--> 15) but is strongly reduced upo n N-acetylation (--> 12). Inversion of stereochemistry at C(5) (--> 14) has little effect on inhibition of beta-glucosidases. These experiments sugges t that 1 acts as an analogue of a protonated beta-glucoside.