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Synthesis of 1,2[ 3 H]‐1,2‐epoxy analogue of fructose‐6P, an affinity label of escherichia coli glucosamine‐6P synthase
Author(s) -
Leriche Caroline,
René Loïc,
Derouet Florence,
Rousseau Bernard,
Badet Bernard
Publication year - 1995
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580361111
Subject(s) - chemistry , aldolase a , dihydroxyacetone phosphate , isomerase , yield (engineering) , triosephosphate isomerase , atp synthase , biochemistry , borohydride , glucosamine , stereochemistry , fructose , dihydroxyacetone , escherichia coli , enzyme , materials science , metallurgy , gene , catalysis , glycerol
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.