Synthesis of 1,2[3H]‐1,2‐epoxy analogue of fructose‐6P, an affinity label of escherichia coli glucosamine‐6P synthase

Abstract

Abstract1,2‐anhydroglucitol‐6P, a known inhibitor of glucose‐6P isomerase, behaved as a fructose‐6P site‐directed irreversible inhibitor of bacterial glucosamine‐6P synthase. The lack of reproducibility of the aldolase‐mediated condensation of dihydroxyacetone phosphate and glycidaldehyde followed by borohydride reduction previously described prompted us to develop a chemical route to this compound and its radiolabelled counterpart. The compound was synthesized in 13 steps from D‐arabinose with a 6% overall yield. Tritium introduction was performed at step 11 (3 → 4) allowing isolation of the title compound of high specific radioactivity.