A new NADPH-dependent benzil reductase (KRED1-Pglu) was identified from the genome of the non-conventional yeast Pichia glucozyma CBS 5766 and overexpressed in E. coli. The new protein was characterised and reaction parameters were optimised for the enantioselective reduction of benzil to (S)-benzoin. A thorough study of the substrate range of KRED1-Pglu was conducted; in contrast to most other known ketoreductases, KRED1-Pglu prefers space-demanding substrates, which are often converted with high stereoselectivity. A molecular modelling study was carried out for understanding the structural determinants involved in the stereorecognition experimentally observed and unpredictable on the basis of steric properties of the substrates. As a result, a new useful catalyst was identified, enabling the enantioselective preparation of different aromatic alcohols and hydroxyketones.
Stereoselective reduction of aromatic ketones by a new ketoreductase from Pichia glucozyma / M.L. Contente, I. Serra, M. Brambilla, I. Eberini, E. Gianazza, V. de Vitis, F. Molinari, P. Zambelli, D. Romano. - In: APPLIED MICROBIOLOGY AND BIOTECHNOLOGY. - ISSN 0175-7598. - 100:1(2016), pp. 193-201. [10.1007/s00253-015-6961-y]
Stereoselective reduction of aromatic ketones by a new ketoreductase from Pichia glucozyma
M.L. ContentePrimo
;I. SerraSecondo
;I. Eberini;E. Gianazza;V. de Vitis;F. Molinari;P. ZambelliPenultimo
;D. Romano
2016
Abstract
A new NADPH-dependent benzil reductase (KRED1-Pglu) was identified from the genome of the non-conventional yeast Pichia glucozyma CBS 5766 and overexpressed in E. coli. The new protein was characterised and reaction parameters were optimised for the enantioselective reduction of benzil to (S)-benzoin. A thorough study of the substrate range of KRED1-Pglu was conducted; in contrast to most other known ketoreductases, KRED1-Pglu prefers space-demanding substrates, which are often converted with high stereoselectivity. A molecular modelling study was carried out for understanding the structural determinants involved in the stereorecognition experimentally observed and unpredictable on the basis of steric properties of the substrates. As a result, a new useful catalyst was identified, enabling the enantioselective preparation of different aromatic alcohols and hydroxyketones.File | Dimensione | Formato | |
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