Production of chiral hydroxy long chain fatty acids by whole cell biocatalysis of pentadecanoic acid with an E. coli recombinant containing cytochrome P450BM-3 monooxygenase

Add time:07/19/2019    Source:sciencedirect.com

A multi-step product recovery process for 12-, 13- and 14-hydroxypentadecanoic acids was developed. Biotransformation of pentadecanoic acid by whole cells of recombinant E. coli K27 (pCYP102, pGEc47), synthesizing cytochrome P450BM-3 monooxygenase [EC 1.14.14.1], led to the production of 12-, 13- and 14-hydroxypentadecanoic acids. To prevent further oxidation of these products, the conversion was performed under oxygen-limited conditions. After filtration and hexane extraction of culture supernatants, the hydroxy fatty acids were methylated. The purification process allowed us to separate the mixture of 12-, 13- and 14-hydroxypentadecanoic acid methyl esters into their single regioisomers by reversed-phase HPLC, followed by precipitation of the compounds as white crystals at 4°C and −20°C. The purified hydroxymethyl esters were characterized by GC–MS analysis.Chiral HPLC analysis of the ω-1 product, 14-hydroxypentadecanoic acid methyl ester, indicated that pentadecanoic acid is oxidized by cytochrome P450BM-3 to optically pure (S)-(+)-14-hydroxypentadecanoic acid at an e.e. of over 95%. This result confirms recent observations by Capdevila[1]that oxidation by cytochrome P450BM-3 monooxygenase is highly stereoselective.

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