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: 1.72). 06/2010; 22(6):543-7. DOI: 10.1002/chir.20775
Source: PubMed

ABSTRACT 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.

  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Lactobacillus brevis alcohol dehydrogenase (Lb-ADH) catalyzes reduction of prochiral carbonyl compounds to chiral alcohol and meanwhile consumes its cofactor NADH into NAD(+), while the cofactor regeneration can be catalyzed by Candida boidinii formate dehydrogenase (Cb-FDH). This work presents three different Escherichia coli whole-cell biocatalyst systems expressing recombinant ADH/FDH, FDH-LIN1-ADH and FDH-LIN2-ADH, respectively, all of which display very high efficacies of prochiral carbonyl conversion with respect to conversion rates and enantiomeric excess values. ADH/FDH represents co-expression of Lb-ADH and Cb-FDH under different promoters in a single vector. Fusion of Lb-ADH and Cb-FDH by a linker peptide LIN1 (GGGGS)2 or LIN2 (EAAAK)2 generates the two bifunctional enzymes FDH-LIN1-ADH and FDH-LIN2-ADH, which enable efficient asymmetric reduction of prochiral ketones in whole-cell biotransformation.
    Scientific Reports 10/2014; 4:6750. DOI:10.1038/srep06750 · 5.08 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 · 2.14 Impact Factor
  • 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.