AI Article Synopsis
- The study outlines a one-pot reaction that combines two enzymatic processes: a stereoselective bioreduction of 2-oxocycloalkanecarbonitriles and nitrile hydrolysis.
- The initial step involves ketoreductases achieving a dynamic reductive kinetic resolution, yielding 2-hydroxycycloalkanenitriles with high enantiomeric and diastereomeric purity.
- Finally, whole cells of Rhodococcus rhodochrous facilitate the conversion to 2-hydroxycycloalkanecarboxylic acids, resulting in excellent overall yields and optical purity.
Article 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.
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| http://dx.doi.org/10.1021/acs.orglett.6b01510 | DOI Listing |
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Article Synopsis
- The study outlines a one-pot reaction that combines two enzymatic processes: a stereoselective bioreduction of 2-oxocycloalkanecarbonitriles and nitrile hydrolysis.
- The initial step involves ketoreductases achieving a dynamic reductive kinetic resolution, yielding 2-hydroxycycloalkanenitriles with high enantiomeric and diastereomeric purity.
- Finally, whole cells of Rhodococcus rhodochrous facilitate the conversion to 2-hydroxycycloalkanecarboxylic acids, resulting in excellent overall yields and optical purity.
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