SYNTHESIS OF 1,2[H-3]-1,2-EPOXY ANALOG OF FRUCTOSE-6P, AN AFFINITY LABEL OF ESCHERICHIA-COLI GLUCOSAMINE-6P SYNTHASE

1,2-anhydroglucitol-6P, a known inhibitor of glucose-6P isomerase, beh aved as a fructose-6P site-directed irreversible inhibitor of bacteria l glucosamine-6P synthase. The lack of reproducibility of the aldolase -mediated condensation of dihydroxyacetone phosphate and glycidaldehyd e followed by borohydride reduction previously described prompted us t o develop a chemical route to this compound and its radiolabelled coun terpart. The compound was synthesized in 13 steps from D-arabinose wit h a 6% overall yield. Tritium introduction was performed at step 11 (( 3) under bar --> (4) under bar) allowing isolation of the title compou nd of high specific radioactivity.