THE FIRST EXAMPLE OF A 6-C-ARYL-D-GLUCOSE - INHIBITION OF GLUCOKINASE

The synthesis of the epimeric 6-C-phenylglucoses is reported; these ar e 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-a ryl-carbohydrates may provide a new range of sugar mimics that control enzymes associated with formation, hydrolysis and other fates of suga r-6-phosphates. X-ray of 6-C-phenyl-L-glycero-beta-D-gluco-hexopyranos e and propylidene-1,5-oxa-2-phenyl-bicyclo-[3.3.0]octane are reported. Copyright (C) 1996 Elsevier Science Ltd