학술논문

Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles.
Document Type
Article
Source
Organic Letters. Jul2016, Vol. 18 Issue 14, p3366-3369. 4p.
Subject
*REDUCTION of ketones
*NITRILES
*HYDROLYSIS
*CARBONITRILES
*STEREOSELECTIVE reactions
*RHODOCOCCUS rhodochrous
Language
ISSN
1523-7060
Abstract
A stereoselective bioreduction of 2-oxocycloalkanecarbonitriles was concurrently coupled to a whole cell-catalyzed nitrile hydrolysis in one-pot. The first step, mediated by ketoreductases, involved a dynamic reductive kinetic resolution, which led to 2-hydroxycycloalkanenitriles in very high enantio- and diastereomeric ratios. Then, the simultaneous exposure to nitrile hydratase and amidase from whole cells of Rhodococcus rhodochrous provided the corresponding 2-hydroxycycloalkanecarboxylic acids with excellent overall yield and optical purity for the all-enzymatic cascade. [ABSTRACT FROM AUTHOR]