Jump to main content
Jump to site search

Issue 6, 2015
Previous Article Next Article

E. coli cells expressing the Baeyer–Villiger monooxygenase ‘MO14’ (ro03437) from Rhodococcus jostii RHA1 catalyse the gram-scale resolution of a bicyclic ketone in a fermentor

Author affiliations

Abstract

The Baeyer–Villiger monooxygenase (BVMO) ‘MO14’ from Rhodococcus jostii RHA1, is an enantioselective BVMO that catalyses the resolution of the model ketone substrate bicyclo[3.2.0]hept-2-en-6-one to the (1S,5R)-2-oxa lactone and the residual (1S,5R)-substrate enantiomer. This regio-plus enantioselective behaviour is highly unusual for BVMOs, which often perform enantiodivergent biotransformations of this substrate. The scaleability of the transformation was investigated using fermentor-based experiments, in which variables including gene codon optimisation, temperature and substrate concentration were investigated. E. coli cells expressing MO14 catalysed the resolution of bicyclo[3.2.0]hept-2-en-6-one to yield (1S,5R)-2-oxa lactone of >99% ee and (1S,5R)-ketone of 96% ee after 14 h at a temperature of 16 °C and a substrate concentration of 0.5 g L−1 (4.5 mM). MO14 is thus a promising biocatalyst for the production of enantio-enriched ketones and lactones derived from the [3.2.0] platform.

Graphical abstract: E. coli cells expressing the Baeyer–Villiger monooxygenase ‘MO14’ (ro03437) from Rhodococcus jostii RHA1 catalyse the gram-scale resolution of a bicyclic ketone in a fermentor

Back to tab navigation

Supplementary files

Article information


Submitted
09 Jul 2014
Accepted
05 Dec 2014
First published
05 Dec 2014

Org. Biomol. Chem., 2015,13, 1897-1903
Article type
Paper
Author version available

E. coli cells expressing the Baeyer–Villiger monooxygenase ‘MO14’ (ro03437) from Rhodococcus jostii RHA1 catalyse the gram-scale resolution of a bicyclic ketone in a fermentor

B. D. Summers, M. Omar, T. O. Ronson, J. Cartwright, M. Lloyd and G. Grogan, Org. Biomol. Chem., 2015, 13, 1897
DOI: 10.1039/C4OB01441C

Social activity

Search articles by author

Spotlight

Advertisements