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Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining beta-glycosidases

TitlePhosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining beta-glycosidases
Publication TypeJournal Article
Year of Publication2014
AuthorsRempel, BP, Withers, SG
JournalORGANIC & BIOMOLECULAR CHEMISTRY
Volume12
Pagination2592-2595
Date PublishedAPR 28
ISSN1477-0520
Abstract

2-Deoxy-2-fluoroglycosides bearing dibenzyl phosphate and phosphonate aglycones were synthesised and tested as covalent inactivators of several retaining alpha- and beta-glycosidases. beta-D-Gluco-, -manno- and -galacto-configured benzyl-benzylphosphonate derivatives efficiently inactivated beta-gluco-, beta-manno- and beta-galactosidases, while alpha-gluco- and alpha-manno-configured phosphate and phosphonate derivatives served instead as slow substrates.

DOI10.1039/c4ob00235k