An Engineered Cholesterol Oxidase Catalyses Enantioselective Oxidation of Non-steroidal Secondary Alcohols.

Chembiochem

Department of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN, Manchester, UK.

Published: April 2022

The enantioselective oxidation of 2° alcohols to ketones is an important reaction in synthetic chemistry, especially if it can be achieved using O -driven alcohol oxidases under mild reaction conditions. However to date, oxidation of secondary alcohols using alcohol oxidases has focused on activated benzylic or allylic substrates, with unactivated secondary alcohols showing poor activity. Here we show that cholesterol oxidase (EC 1.1.3.6) could be engineered for activity towards a range of aliphatic, cyclic, acyclic, allylic and benzylic secondary alcohols. Additionally, since the variants demonstrated high (S)-selectivity, deracemisation reactions were performed in the presence of ammonia borane to obtain enantiopure (R)-alcohols.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9303356PMC
http://dx.doi.org/10.1002/cbic.202200075DOI Listing

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