Biocatalysis are fascinating with the recent advances in enzyme engineering and metabolic engineering technologies. Biotransformations with multi-step enzymatic reactions are enhancing biocatalytic efficiency and expanding the utility of biocatalysis. For example, chiral amines and lactones were prepared in high yields through several enzyme cascade reactions from alcohols. However, it is difficult to produce bulky aliphatic amines by either enzymatic or chemical means. Thus, we have investigated enzyme cascade reactions to produce bulky aliphatic amino fatty acids from renewable fatty acids. (Z)-12-Aminooctadec-9-enoic acid was prepared via (Z)-12-ketooctadec-9-enoic acid from ricinoleic acid ((Z)-12-hydroxyoctadec-9-enoic acid) with a conversion of 71% by an in vivo two-step biotransformation employing a long chain secondary alcohol dehydrogenase (SADH) from Micrococcus luteus and a variant of the amine transaminase (ATA) from Vibrio fluvialis. 10-Aminooctadecanoic acid was also produced via 10-hydroxyoctadecanoic acid and 10-ketooctadecanoic acid from oleic acid ((Z)-octadec-9-enoic acid) by an in vivo three-step biotransformation employing not only the SADH and ATA variants, but also a fatty acid double bond hydratase (OhyA) from Stenotrophomonas maltophilia. 10-Aminooctadecanoic acid was produced at a total rate of 4.4 U/g dry cells with a conversion of 87% by recombinant Escherichia coli expressing the SADH and ATA variants, and OhyA simultaneously. In addition, bulky aliphatic amino fatty acids could also be introduced by the isolated enzymes (i. e., the SADH, the ATA variants, and a nicotinamide adenine dinucleotide (NADH) oxidase from Lactobacillus brevis) with methylbenzylamine or benzylamine as an amino donor. This study contributes to the biosynthesis of long chain aliphatic amino fatty acids containing two large substituents next to the amino functional group.

Biocatalytic synthesis of amino fatty acids

2019 Fall National Meeting

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