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Fate of the Oxygen Atoms in the Diol-Dehydratase-Catalyzed Dehydration of meso-Butane-2,3-diol

✍ Scribed by Giovanna Speranza; Carlo F. Morelli; Maximilian Orlandi; Mauro Scarpellini; Paolo Manitto

Publisher
John Wiley and Sons
Year
2001
Tongue
German
Weight
111 KB
Volume
84
Category
Article
ISSN
0018-019X

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✦ Synopsis

18 O-Substituted propane-1,2-diols and meso-butane-1,2-diols were synthesized and fed to growing cells of Lactobacillus brevis. Propan-1-ol and butan-2-ol, prepared from such diols through diol-dehydratase-catalyzed dehydration followed by intracellular reduction, were analyzed for their 18 O-content. For each propane-1,2-diol enantiomer, partial retention or complete loss of the isotope appeared to be related to the mode of substrate binding. Specific retention of the O-atom linked to the (R)-configured C-atom of meso-butane-1,2-diol indicates that the diol dehydratase handles this substrate like (R)-propane-1,2-diol.

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