|Title||Non-Stick Sugars: Synthesis of Difluorosugar Fluorides as Potential Glycosidase Inactivators|
|Publication Type||Journal Article|
|Year of Publication||2009|
|Authors||Rempel, BP, Withers, SG|
|Journal||AUSTRALIAN JOURNAL OF CHEMISTRY|
Four new difluorosugar fluorides, 2-deoxy-2,5-difluoro-alpha-L-idopyranosyl fluoride, 1,5-difluoro-D-glucopyranosyl fluoride, 1,5-difluoro-L-idopyranosyl fluoride, and 2-deoxy-1,2-difluoro-D-glucopyranosyl fluoride, were synthesized from known precursors by a radical bromination/fluoride displacement sequence, followed by deprotection. The compounds were tested as time-dependent inactivators of the beta-glucosidase from Agrobacterium sp. (Abg, EC 184.108.40.206) and, while they were shown to bind to the enzyme active site as reversible competitive inhibitors, the only time-dependent inactivation observed was traced to the presence of an extremely small amount (<0.1%) of a highly reactive contaminating impurity.