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Catalysts 2015, 5(4), 2068-2084; doi:10.3390/catal5042068

Microbial Stereoselective One-Step Conversion of Diols to Chiral Lactones in Yeast Cultures

Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland
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Academic Editor: Keith Hohn
Received: 5 November 2015 / Revised: 25 November 2015 / Accepted: 30 November 2015 / Published: 8 December 2015
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Abstract

It has been shown that whole cells of different strains of yeast catalyze stereoselective oxidation of meso diols to the corresponding chiral lactones. Among screening-scale experiments, Candida pelliculosa ZP22 was selected as the most effective biocatalyst for the oxidation of monocyclic diols 3a–b with respect to the ratio of high conversion to stereoselectivity. This strain was used in the preparative oxidation, affording enantiomerically-enriched isomers of lactones: (+)-(3aR,7aS)-cis-hexahydro-1(3H) -isobenzofuranone (2a) and (+)-(3aS,4,7,7aR)-cis-tetrahydro-1(3H)-isobenzofuranone (2b). Scaling up the culture growth, as well as biotransformation conditions has been successfully accomplished. Among more bulky substrates, bicyclic diol 3d was totally converted into enantiomerically-pure exo-bridged (+)-(3aR,4S,7R,7aS)-cis-tetrahydro-4,7-methanoisobenzofuran -1(3H)-one (2d) by Yarrovia lipolytica AR71. Microbial oxidation of diol 3f by Candida sake AM908 and Rhodotorula rubra AM4 afforded optically-pure cis-3-butylhexahydro-1(3H) -isobenzofuranone (2f), however with low conversion. View Full-Text
Keywords: biooxidation; yeast; lactones; diols; stereoselectivity; scaling up biooxidation; yeast; lactones; diols; stereoselectivity; scaling up
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Boratyński, F.; Szczepańska, E.; Pannek, J.; Olejniczak, T. Microbial Stereoselective One-Step Conversion of Diols to Chiral Lactones in Yeast Cultures. Catalysts 2015, 5, 2068-2084.

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