Production of (R)-1-phenylethanols Through Bioreduction of Acetophenones by a New Fungus Isolate Trichothecium roseum

Faculty of Sciences, Department of Chemistry, Ataturk University, Erzurum 25240, Turkey.
Chirality (Impact Factor: 1.89). 06/2010; 22(6):543-7. DOI: 10.1002/chir.20775
Source: PubMed


A total of 120 fungal strains were isolated from soil samples and evaluated in the bioreduction of substituted acetophenones to the corresponding (R)-alcohols. Among these strains, isolate Trichothecium roseum EBK-18 was highly effective in the production of (R)-alcohols with excellent enantioselectivity (ee > 99%). Gram scale preparation of (R)-1-phenylethanol is reported.

Full-text preview

Available from:
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: This database, available online, reviews 876 published accounts and presents a list of species representing the genera Aspergillus, Penicillium and related species in Turkey. Aspergillus niger, A. fumigatus, A. flavus, A. versicolor and Penicillium chrysogenum are the most common species in Turkey, respectively. According to the published records, 428 species have been recorded from various subtrates/habitats in Turkey.
  • [Show abstract] [Hide abstract]
    ABSTRACT: Biocatalysts that can specifically catalyze the transformations of fluorinated compounds are rare. A novel NADPH-dependent fluorinated ketone reductase that reduces trifluoroacetophenone to (S)-trifluorophenylethanol with excellent enantioselectivity (ee > 99%) from Geotrichum candidum NBRC 5767 was isolated, purified, and characterized. Through ammonium sulfate fractionation and several chromatographies, this enzyme was purified to 95-fold with 3.5% yield. Gel filtration chromatography with SDS-PAGE revealed this protein to be a dimer of 60 kDa subunits. An investigation of the substrate specificity of the purified enzyme revealed that it was highly selective for ketones containing fluorines at the α position.
    Biochemical Engineering Journal 07/2013; 76:13–16. DOI:10.1016/j.bej.2013.04.005 · 2.47 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Fluorinated 1-arylethanols are important building blocks in medicinal chemistry especially for preparing kinase inhibitors for cancer therapy, NK1 receptor antagonists and drugs used in treatment of osteoporosis. Asymmetric reduction of carbonyl groups using enzymes is one of the key technologies to obtain such molecules in enantiomerically pure form. By using isolated enzymes coupled with cofactor recycling, highly concentrated, robust and economical processes can be developed. The aim of this review is to give an overview of biocatalytic carbonyl reduction with special focus on processing of fluoro containing 1-arylethanones with enzymes in cell free systems. The methodologies applied to improve the reactions are highlighted, alongside potential application of the building blocks in bioactive compounds. Enzymatic ketone reduction is concluded to be most beneficial as compared to chemo catalytic methods in transformations of highly fluorinated and therefore electron deficient ketones. A high enantiomeric excess can be achieved, and by changing the catalyst, both enantiomers are accessible. High rates are often seen for such electron deficient ketones, and the reactions have a favourable equilibrium position.
    Bioorganic Chemistry 09/2013; 51C:31-47. DOI:10.1016/j.bioorg.2013.09.003 · 2.15 Impact Factor
Show more