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Highly enantiomeric reduction of acetophenone and its derivatives by locally isolated Rhodotorula glutinis
Author(s) -
Zilbeyaz Kani,
Kurbanoglu Esabi B.
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20846
Subject(s) - acetophenone , rhodotorula , chemistry , biocatalysis , enantioselective synthesis , enantiomer , enantiomeric excess , yeast , yield (engineering) , stereochemistry , chirality (physics) , organic chemistry , catalysis , reaction mechanism , biochemistry , materials science , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , metallurgy
Ninety isolates of microorganisms belonging to different taxonomical groups (30 bacteria, 20 yeast, and 40 fungi) were previously isolated from various samples. These isolates were screened as reducing agents for acetophenone 1a to phenylethanol 2a . It was found that the isolate EBK‐10 was the most effective biocatalyst for the enantioselective bioreduction of acetophenone. This isolate was identified as Rhodotorula glutinis by the VITEK 2 Compact system. The various parameters (pH 6.5, temperature 32°C, and agitation 200 rpm) of the bioreduction reaction was optimized, which resulted in conversions up to 100% with >99% enantiomeric excesses (ee) of the S ‐configuration. The preparative scale bioreduction of acetophenone 1a by R. glutinis EBK‐10 gave ( S )‐1‐phenylethanol 2a in 79% yield, complete conversion, and >99% ee. In addition, R.glutinis EBK‐10 successfully reduced various substituted acetophenones. Chirality, 2010. © 2010 Wiley‐Liss, Inc.