Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases
1Department of Chemistry, University of British Columbia, Vancouver, B.C. V6 T 1Z1, Canada. withers@chem.ubc.ca.
Organic & Biomolecular Chemistry
|March 13, 2014
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.
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