Candida zeylanoides as whole-cell biocatalyst to perform asymmetric bioreduction of benzophenone derivatives

Abstract

Candida zeylanoides P1 was investigated as whole cell biocatalyst for the bioreduction of biaryl prochiral ketones into chiral carbinols, which can be used as pharmaceutical intermediate. Bioreduction of different biaryl ketones was carried out to their corresponding chiral biaryl carbinols such as (S)-(4-chlorophenyl) (phenyl) methanol (2a), which can be used in the synthesis of L-cloperastine drug, with antitussive, antiepidemic activity and bronchial musculature relaxant characteristics, in gram scale, enantiopure form (>99%) and excellent yields. The selectivity of C. zeylanoides P1 in enantioselective reduction of biaryl ketones was not affected by the steric and electronic effects of substrates. The current method demonstrates an encouraging green chemistry approach for the production of biaryl secondary chiral alcohols of pharmaceutical importance in mild, inexpensive and environmentally friendly process. The present study has many benefits since this yeast biocatalyst were successfully applied bioreduction of structurally bulky prochiral substrates, which cannot be reducted by chemical catalysis.

GRAPHICAL ABSTRACT

Keywords:

• Chirality
• Candida zeylanoides
• chiral benzophenone carbinols
• enantioselective reduction
• (S)-(4-chlorophenyl) (phenyl) methanol

Acknowledgements

We are grateful to Bayburt University Central Research Laboratory for HPLC analysis and and Dr. Enes DERTLİ (Bayburt University) for providing yeast strain used in this study.

Data availability

The data that support the findings of this study are openly available in https://doi.org/10.1002/cbdv.201700121, reference number.^[34]

Spectroscopic datas, copies of ¹H, ¹³C NMR spectra, substrate, chiral, and racemic HPLC chromatograms of 1a–3a related to this article can be found at supplementary data.