Biosynthesis of Medium- to Long-Chain α,ω-Diols from Free Fatty Acids Using CYP153A Monooxygenase, Carboxylic Acid Reductase, and E. coli Endogenous Aldehyde Reductases

Abstract

α,ω-Diols are important monomers widely used for the production of polyesters and polyurethanes. Here, biosynthesis of α,ω-diols (C 8-C 16) from renewable free fatty acids using CYP153A monooxygenase, carboxylic acid reductase, and E. coli endogenous aldehyde reductases is reported. The highest yield of α,ω-diol was achieved for the production of 1,12-dodecanediol. In the nicotinamide adenine dinucleotide phosphate (NADPH) cofactor regeneration system, 5 g/L of 1,12-dodecanediol was synthesized in 24 h reaction from the commercial ω-hydroxy dodecanoic acid. Finally, 1.4 g/L 1,12-dodecanediol was produced in a consecutive approach from dodecanoic acids. The results of this study demonstrated the scope of the potential development of bioprocesses to substitute the petroleum-based products in the polymer industry.

Kinetic Resolution of Racemic Amines to Enantiopure (S)-amines by a Biocatalytic Cascade Employing Amine Dehydrogenase and Alanine Dehydrogenase

“…Therefore, to catalyze the efficient kinetic resolution of racemic amines, recombinant E. coli cells expressing AmDHs and AlaDH were used as whole-cell biocatalysts. Whole cell biotransformation systems constituting two or more cells, each expressing different protein, may impose the mass transfer limitations [56,57]. In order to develop a single-cell system expressing AmDH and AlaDH, the genes encoding Chi-AmDH-AlaDH and AlaDH were cloned into pET-24ma and pET-Duet vectors, respectively [Since the substrate scope of Chi-AmDH-AlaDH is much better than Rs-AmDH, we only used Chi-AmDH-AlaDH whole cell system].…”

Biosynthesis of Nylon 12 Monomer, ω-Aminododecanoic Acid Using Artificial Self-Sufficient P450, AlkJ and ω-TA

“…Analytical conditions for free fatty acids and their derivatives using gas chromatography are well established and reported in our previously published reports [4,7,[10][11][12]20]. Quantitative analysis was performed using a gas chromatography instrument with a flame ionization detector (GC/FID) fitted with an AOC-20i series auto sampler injector (GC 2010 plus Series, Shimadzu Scientific Instruments, Kyoto 604-8511, Japan).…”

“…Production of biochemicals from vegetable oil derivatives (e.g., free fatty acids (FFAs)) have drawn great attention as an alternative means to develop sustainable and green production processes, known as biorefinery [1][2][3][4]. Fatty acids and fatty acid derivatives are employed for the production of various polymer intermediates and precursors with broad commercial and pharmaceutical implications, including cosmetics, adhesives, lubricants, surfactants, coatings, biofuels, and anticancer agents [5][6][7].…”

Biocatalysis and Biotransformations

“…Acosta and coworkers reported the synthesis of purine derivatives by the sequential action of 2 -deoxyribosyltransferases and hypoxanthine-guanine-xanthine phosphoribosyltransferases [14]. The utilization of renewable free fatty acids as a source of α,ω-diols (C 8 -C 16 ) by the action of CYP153A monooxygenase, carboxylic acid reductase, and aldehyde reductases was demonstrated by Ahsan and coworkers [15]. Huang and coworkers investigated the synthesis of 2-ethylhexyl salicylate using lipases [16].…”