title: Potential of some yeast strains in the stereoselective synthesis of (R)-(-)-phenylacetylcarbinol and (S)-(+)-phenylacetylcarbinol and their reduced 1,2-dialcohol derivatives.
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.
authors.affiliation: Departament de Química Orgànica, Facultat de Farmàcia, Universitat de València (UVEG), Vicent Andrés Estellés s/n, 46100, Burjassot, València, Spain, cecilia.andreu@uv.es.
authors.forename: Cecilia
authors.initials: C
authors.lastname: Andreu
authors.forename: Marcel Lí
authors.initials: ML
authors.lastname: Del Olmo
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000378:metabolism; D001711:Biotransformation; D003470:Culture Media / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007716:Kluyveromyces / Q000378:metabolism*; D019946:Propylene Glycol / Q000378:metabolism; D004718:Saccharomycetales / Q000378:metabolism*; D013237:Stereoisomerism; D013696:Temperature; D013997:Time Factors
chemical_list: D003470:Culture Media; D000096:Acetone; D019946:Propylene Glycol; C035293:1-hydroxy-1-phenyl-2-propanone