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Production of ( R )‐3′‐fluorophenylethan‐1‐ol by Trichothecium roseum isolate in a laboratory scale bioreactor
Author(s) -
Kurbanoglu E.B.,
Taskin M.,
Zilbeyaz K.,
Kurbanoglu N.I.
Publication year - 2009
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.2204
Subject(s) - chemistry , fermentation , biocatalysis , enantiomer , bioreactor , enantiomeric excess , organic chemistry , nuclear chemistry , enantioselective synthesis , catalysis , ionic liquid
BACKGROUND: Enantiomerically pure, fluorinated compounds play an important role in medicinal chemistry. Trichothecium roseum strains were isolated for the production of ( R )‐3′‐fluorophenylethan‐1‐ol. Biocatalytic production of optically active ( R )‐3′‐fluorophenylethan‐1‐ol was achieved by asymmetric reduction of 3′‐fluoroacetophenone in a batch culture of Trichothecium roseum using ram horn peptone (RHP). The reaction conditions (pH, temperature and agitation) required to improve the conversion of 3′‐fluoroacetophenone and enantiomeric excess ( ee ) of ( R )‐3′‐fluorophenylethan‐1‐ol were studied. RESULTS: The gram scale production of ( R )‐3′‐fluorophenylethan‐1‐ol by the most effective biocatalyst, Trichothecium roseum EBK‐11 using RHP was carried out in a fermenter with 1 L working volume. The results showed that the yield with >99% ee of ( R )‐3′‐fluorophenylethan‐1‐ol reached 77%. The concentration of ( R )‐3′‐fluorophenylethan‐1‐ol at the end of 62 h fermentation was 2.70 g L −1 . CONCLUSION: An important chiral intermediate for the pharmaceutical industry using T. roseum EBK‐11 in submerged culture containing RHP from waste material was produced up to gram scale with excellent ee (99%). In this work, T. roseum fungus was used for the first time as a biocatalyst for efficient production of a chiral alcohol. Copyright © 2009 Society of Chemical Industry