Production of ( R )‐3′‐fluorophenylethan‐1‐ol by Trichothecium roseum isolate in a laboratory scale bioreactor

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