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Preparation of enantiomerically enriched aromatic β-hydroxynitriles and halohydrins by ketone reduction with recombinant ketoreductase KRED1-Pglu

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논문

Preparation of enantiomerically enriched aromatic β-hydroxynitriles and halohydrins by ketone reduction with recombinant ketoreductase KRED1-Pglu

학술지

Tetrahedron

저자명

Contente, M.L.; Serra, I.; Molinari, F.; Gandolfi, R.; Pinto, A.; Romano, D.

초록

A NADPH-dependent benzil reductase (KRED1-Pglu) was used as recombinant enzyme for catalysing the reduction of different functionalised ketones. The reactions were carried out in the presence of a catalytic amount of NADP<SUP>+</SUP> and an enzyme-coupled transformation (oxidation of glucose catalysed by glucose dehydrogenase), for regenerating the cofactor and thus driving the reaction to completion. KRED1-Pglu showed remarkable versatility, being able to reduce different &beta;-ketonitriles and &alpha;-haloketones at different pHs; notably, depending on the nature of the substrate, KRED1-Pglu can be used for efficient and clean enzymatic reduction, avoiding side-reactions due to the pH of the medium. The reduction generally occurred with high enantioselectivity, allowing the preparation of enantiomerically enriched &beta;-hydroxynitriles and halohydrins in high yields; the stereochemical outcome of the reduction followed in all the cases the so-called Prelog's rule.

발행연도

2016

발행기관

Pergamon Press

ISSN

0040-4020

ISSN

1464-5416

72

27

페이지

pp.3974-3979

주제어

Ketoreductase; Stereoselective; Ketone reduction; Pichia glucozyma; Enzymatic reduction

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논문; 2016-07-01

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