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

✍ Scribed by Caroline Leriche; Loïc René; Florence Derouet; Bernard Rousseau; Bernard Badet

Publisher: John Wiley and Sons
Year: 1995
Tongue: French
Weight: 407 KB
Volume: 36
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580361111

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✦ Synopsis

Abstract

1,2‐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.

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