Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones.
Didymosphaeria igniaria is a promising biocatalyst in asymmetric reductions of prochiral aromatic-aliphatic ketones such as acetonaphthones, acetophenones, and acetylpyridines. The organism converted the substrates mainly to (S)-alcohols. Excellent results in terms of conversion and enantioselectivity (100% yield, >99% ee) were obtained with acetonaphthones. In case of acetyl pyridines, the optical purity of the product depended on the position of the carbonyl group on the pyridine ring and followed the order 2-acetyl ≫ 4-acetyl > 3-acetyl-pyridine. Transformation of o-methoxy-acetophenone gave optically pure (S)-(-)-1-(2-methoxyphenyl)-ethanol in 95% yield. The transformation of para-methyl ketone gave (R)-alcohol (81% ee), whereas para-bromo ketone gave (S)-alcohol (98% ee). Monitoring of the biotransformation of these substrates over time led to the conclusion that for both substrates, non-selective carbonyl group reduction occurred in the first step, followed by selective oxidation of the (R)-isomer of p-bromo-phenylethanol and selective oxidation of the (S)-isomer of p-methyl-phenylethanol. D. igniaria exhibited poor enantioselectivity in the reduction of bicyclic aryl-aliphatic ketones such as 1- and 2-tetralones. Only (S)-5-methoxy-1-tetralol was obtained in optically pure (>99% ee) form.
Świzdor
Alina
A
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland. alina.swizdor@up.wroc.pl
Janeczko
Tomasz
T
Dmochowska-Gładysz
Jadwiga
J
D000098:Acetophenones / Q000378:metabolism*; D000426:Alcohol Dehydrogenase / Q000378:metabolism; D001203:Ascomycota / Q000145:classification* / Q000378:metabolism*; D055162:Biocatalysis; D001711:Biotransformation; D010084:Oxidation-Reduction; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives / Q000378:metabolism; D044024:Tetralones / Q000378:metabolism
C522554:1-(4-bromophenyl)ethanol; D000098:Acetophenones; D044024:Tetralones; D000426:Alcohol Dehydrogenase; D010626:Phenylethyl Alcohol