The first example of a 6-C-aryl-D-glucose: Inhibition of glucokinase

Article abstract of DOI:10.1016/0957-4166(96)00356-4

The synthesis of the epimeric 6-C-phenylglucoses is reported; these are the first compounds with one of the prochiral methylene hydrogens on C-6 of a hexose being replaced by an aryl group. Both isomers inhibit glucokinase and provide further indications that 6-C-alkyl- and 6-C-aryl-carbohydrates may provide a new range of sugar mimics that control enzymes associated with formation, hydrolysis and other fates of sugar-6-phosphates. X-ray crystal structures of 6-C-phenyl-L-glycero-β-D-gluco-hexopyranose and (2R,3S,4R,6R,7R,8S)2,3,6,7-tetrahydroxy-6,7-O-isopropylidene-1,5-oxa-2 -phenyl-bicyclo-[3.3.0]octane are reported.