화학공학소재연구정보센터
Bioresource Technology, Vol.118, 306-314, 2012
Bioreduction of methyl heteroaryl and aryl heteroaryl ketones in high enantiomeric excess with newly isolated fungal strains
Enantioenriched heteroaryl ethanols and aryl heteroarylmethanols are important intermediates and structural motifs in medicinal chemistry. Asymmetric biocatalytic reduction of corresponding ketones provides a straightforward approach for preparation of these compounds. Accordingly, three newly isolated fungal strains have been described, which produced the desired heteroaryl alcohols in high enantiomeric excess (ee). A broad substrate specificity was observed within these limited number of biocatalysts as demonstrated by preparation of a variety of heteroaryl alcohols, including (S)-5-(1-hydroxyethyl)furo[2,3-c]pyridine, a key intermediate for HIV-1 reverse transcriptase inhibitor, (5)phenyl(pyridin-2-yl)methanol, an analgesic and (S,S)-2,6-bis(1-hydroxyethyl)pyridine, a chiral building block, mostly in >99% ee and 80-92% yield. Micro-morphologically, one of the isolate was found to be similar to Penicillium funiculosum. However, its beta-tubulin sequence showed only 88% sequence identity with the known beta-tubulin sequences of Penicillium. It may, therefore, represent a new species of Penicillium. The other biocatalysts were identified as Alternaria alternate and Talaromyces flavus. (C) 2012 Elsevier Ltd. All rights reserved.