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One‐pot Conversion of Cycloalkanes to Lactones
Author(s) -
Pennec Alizé,
Hollmann Frank,
Smit Martha S.,
Opperman Diederik J.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402835
Subject(s) - monooxygenase , chemistry , cofactor , cycloalkane , ketone , cycloheptane , biocatalysis , stereochemistry , cyclooctane , organic chemistry , lactone , baeyer–villiger oxidation , catalysis , cytochrome p450 , enzyme , cyclohexane , reaction mechanism
The one‐pot conversion of cycloalkanes to their corresponding lactones was achieved through the use of a synthetic pathway consisting of a cytochrome P450 monooxygenase (CYP450) for initial oxyfunctionalization of the cycloalkane, an alcohol dehydrogenase for ketone production and a Baeyer–Villiger monooxygenase for lactone formation. Through variation of the cofactor dependence of the biocatalysts and the cofactor regeneration system, final product concentrations of nearly 3 g L −1 enantholactone (2‐oxocanone) from cycloheptane was reached within 12 h with a total turnover number (TTN) of 4185 with respect to the CYP450.