DNA from beach-washed shells of the ram's horn squid, Spirula spirula

Abstract

<jats:title>Abstract</jats:title><jats:p><jats:bold>BACKGROUND:</jats:bold> Enantiomerically pure, fluorinated compounds play an important role in medicinal chemistry. <jats:italic>Trichothecium roseum</jats:italic> strains were isolated for the production of (<jats:italic>R</jats:italic>)‐3′‐fluorophenylethan‐1‐ol. Biocatalytic production of optically active (<jats:italic>R</jats:italic>)‐3′‐fluorophenylethan‐1‐ol was achieved by asymmetric reduction of 3′‐fluoroacetophenone in a batch culture of <jats:italic>Trichothecium roseum</jats:italic> using ram horn peptone (RHP). The reaction conditions (pH, temperature and agitation) required to improve the conversion of 3′‐fluoroacetophenone and enantiomeric excess (<jats:italic>ee</jats:italic>) of (<jats:italic>R</jats:italic>)‐3′‐fluorophenylethan‐1‐ol were studied.</jats:p><jats:p><jats:bold>RESULTS:</jats:bold> The gram scale production of (<jats:italic>R</jats:italic>)‐3′‐fluorophenylethan‐1‐ol by the most effective biocatalyst, <jats:italic>Trichothecium roseum</jats:italic> EBK‐11 using RHP was carried out in a fermenter with 1 L working volume. The results showed that the yield with &gt;99% <jats:italic>ee</jats:italic> of (<jats:italic>R</jats:italic>)‐3′‐fluorophenylethan‐1‐ol reached 77%. The concentration of (<jats:italic>R</jats:italic>)‐3′‐fluorophenylethan‐1‐ol at the end of 62 h fermentation was 2.70 g L<jats:sup>−1</jats:sup>.</jats:p><jats:p><jats:bold>CONCLUSION:</jats:bold> An important chiral intermediate for the pharmaceutical industry using <jats:italic>T. roseum</jats:italic> EBK‐11 in submerged culture containing RHP from waste material was produced up to gram scale with excellent <jats:italic>ee</jats:italic> (99%). In this work, <jats:italic>T. roseum</jats:italic> fungus was used for the first time as a biocatalyst for efficient production of a chiral alcohol. Copyright © 2009 Society of Chemical Industry</jats:p>