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The `mirror-image' postulate as a guide to the selection and evaluation of pyrrolidines as alpha-L-fucosidase inhibitors

TitleThe `mirror-image' postulate as a guide to the selection and evaluation of pyrrolidines as alpha-L-fucosidase inhibitors
Publication TypeJournal Article
Year of Publication2013
AuthorsStocker, BL, Jongkees, SAK, Win-Mason, AL, Dangerfield, EM, Withers, SG, Timmer, MSM
JournalCARBOHYDRATE RESEARCH
Volume367
Pagination29-32
Date PublishedFEB 15
ISSN0008-6215
Abstract

The ability of a series of pyrrolidines to inhibit several glycosidases was investigated. Using Fleet's `mirror-image postulate', it was proposed that enantiomeric derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol (a known alpha-D-galactosidase inhibitor) would show inhibitory activity against alpha-L-fucosidases. Some modest alpha-L-fucosidase inhibitory activity was observed for selected compounds (particularly an aminomethyl pyrrolidine) and it was proposed that better activity could be obtained by modifying the C-2 side chain of the pyrrolidine core. The D-galacto carbamate scaffold also exhibited somewhat selective, albeit modest, alpha-L-fucosidase inhibitory activity and may prove to be an interesting scaffold for further development. (C) 2012 Elsevier Ltd. All rights reserved.

DOI10.1016/j.carres.2012.11.011