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- Title
Potential of some yeast strains in the stereoselective synthesis of ( R)-(−)-phenylacetylcarbinol and ( S)-(+)-phenylacetylcarbinol and their reduced 1,2-dialcohol derivatives.
- Authors
Andreu, Cecilia; Olmo, Marcel·lí
- Abstract
Whole cells of different yeast species have been widely used for a number of asymmetric transformations. In the present study, the screening of several yeast strains revealed the utility of Debaryomyces etchellsii in acyloin condensation for ( R)-(−)-phenylacetylcarbinol production. Some conditions for the efficient biotransformation of benzaldehyde and minimization in the production of by-products were explored: pH of the reaction medium, use of additives (ethanol or acetonitrile), temperature, time, and substrate concentration and dosing. The optimal conditions found allowed the transformation of up to 10 g/L of the starting material in reactions carried out at high scale. Furthermore, the yeast Kluyveromyces marxianus was seen to be a convenient biocatalyst to carry out the kinetic resolution by the bioreduction of racemic (+/−)-phenylacetylcarbinol, resulting in ( S)-(+)-phenylacetylcarbinol with excellent stereoselectivity. Finally, the ketone reduction of both isolated stereoisomers ( R and S) by D. etchellsii allowed the obtainment of two of the four diastereoisomers of 1-phenyl-1,2-propanediol. All these compounds are key precursors for the production of interesting pharmaceutical and chemical products.
- Subjects
YEAST fungi biotechnology; STEREOSELECTIVE reaction kinetics; DIASTEREOISOMERS synthesis; BIOCATALYSIS; KLUYVEROMYCES marxianus; BIOTRANSFORMATION in microorganisms; ETHYNYL benzene
- Publication
Applied Microbiology & Biotechnology, 2014, Vol 98, Issue 13, p5901
- ISSN
0175-7598
- Publication type
Article
- DOI
10.1007/s00253-014-5635-5