title: Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases.
abstract: 2-Deoxy-2-fluoroglycosides bearing dibenzyl phosphate and phosphonate aglycones were synthesised and tested as covalent inactivators of several retaining α- and β-glycosidases. β-d-Gluco-, -manno- and -galacto-configured benzyl-benzylphosphonate derivatives efficiently inactivated β-gluco-, β-manno- and β-galactosidases, while α-gluco- and α-manno-configured phosphate and phosphonate derivatives served instead as slow substrates.
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, B.C. V6 T 1Z1, Canada. withers@chem.ubc.ca.
authors.forename: B P
authors.initials: BP
authors.lastname: Rempel
authors.forename: S G
authors.initials: SG
authors.lastname: Withers
mesh_terms: D003837:Deoxy Sugars / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004950:Esterases / Q000737:chemistry* / Q000378:metabolism; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D063065:Organophosphonates / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship; D013403:Sugar Phosphates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D003837:Deoxy Sugars; D063065:Organophosphonates; D013403:Sugar Phosphates; D004950:Esterases; D006026:Glycoside Hydrolases