Journal
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
Volume 17, Issue 6, Pages 235-240Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/S1381-1177(02)00013-9
Keywords
Acetobacter; Gluconobacter; carboxylic acids; resolution; oxidation
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Acetic acid bacteria (five strains of Acetobacter and five strains of Gluconobacter) were used for the biotransformation of different primary alcohols (2-chloropropanol and 2-phenylpropanol) and diols (1,3-butandiol, 1,4-nonandiol and 2,3-butandiol). Most of the tested strains efficiently oxidized the substrates. 2-Chloropropanol and 1,3-butandiol were oxidized with good rates and low enantioselectivity (enantiomeric excess = 18-46% of the S-acid), while microbial oxidation of 2-phenylpropanol furnished (S)-2-phenyl-1-propionic acid with enantiomeric excess (e.e.) >90% with 10 strains. The dehydrogenation of 2,3-butandiol was strongly dependent on the stereochemistry of the substrate; the meso form gave S-acetoin with all the tested strains, the only exception being a Gluconobacter strain. The formation of diacetyl was observed only by using R,R-2,3-butandiol with Acetobacter strains. Oxidation of 1,4-nonandiol gave gamma-nonanoic lactone in one step, although with moderate enantioselectivity. (C) 2002 Elsevier Science B.V. All rights reserved.
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