Premium
Oxidation of threo ‐9,10‐Dihydroxystearic Acid Mediated by Micrococcus luteus as a Key Step in the Conversion of Oleic Acid into Pelargonic and Azelaic Acids
Author(s) -
Colombo Danilo,
Brenna Elisabetta,
Casali Beatrice,
Ghezzi Maria Chiara,
Parmeggiani Fabio,
Tentori Francesca,
Tessaro Davide,
Boratyński Filip
Publication year - 2021
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.202100514
Subject(s) - azelaic acid , micrococcus luteus , oleic acid , chemistry , diol , organic chemistry , micrococcus , aqueous solution , biochemistry , bacteria , biology , genetics , escherichia coli , gene
A sequential one‐pot chemoenzymatic procedure for the conversion of diol 1 , easily obtained from oleic acid, into pelargonic and azelaic acids is herein described. The oxidation of diol 1 into a mixture of the corresponding regioisomeric hydroxyketones was promoted by an alcohol dehydrogenase from Micrococcus luteus , selected after an extensive screening of commercial enzyme kits and strain collections. The stereochemistry of the oxidation process of chiral diol 1 was also investigated. The hydroxyketones obtained by the biocatalyzed oxidation were submitted to further oxidative cleavage by a mild treatment with aqueous NaClO in a biphasic mixture, affording pelargonic and azelaic acids in high yield (76 and 71 %, respectively) with no need of column chromatography.