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Baeyer-Villiger monooxygenases (BVMOs) are able to catalyze regiospecific Baeyer-Villiger oxygenation of a variety of cyclic and linear ketones to generate the corresponding lactones and esters, respectively. However, the enzymes are usually difficult to express in a functional form in microbial cells and are rather unstable under process conditions hindering their large-scale applications. Thereby, we investigated engineering of the BVMO from  Pseudomonas putida  KT2440 and the gene expression system to improve its activity and stability for large-scale biotransformation of ricinoleic acid ( 1 ) into the ester (i.e., ( Z )-11-(heptanoyloxy)undec-9-enoic acid) ( 3 ), which can be hydrolyzed into 11-hydroxyundec-9-enoic acid ( 5 ) (i.e., a precursor of polyamide-11) and  n -heptanoic acid ( 4 ). The polyionic tag-based fusion engineering of the BVMO and the use of a synthetic promoter for constitutive enzyme expression allowed the recombinant  Escherichia coli  expressing the BVMO and the secondary alcohol dehydrogenase of  Micrococcus luteus  to produce the ester ( 3 ) to 85 mM (26.6 g/L) within 5 h. The 5 L scale biotransformation process was then successfully scaled up to a 70 L bioreactor;  3  was produced to over 70 mM (21.9 g/L) in the culture medium 6 h after biotransformation. This study demonstrated that the BVMO-based whole-cell reactions can be applied for large-scale biotransformations.

scientific reports

Engineering of Baeyer-Villiger monooxygenase-based Escherichia coli biocatalyst for large scale biotransformation of ricinoleic acid into (Z)-11-(heptanoyloxy)undec-9-enoic acid