Enzymatic Synthesis of ω-Hydroxydodecanoic Acid By Employing a Cytochrome P450 from Limnobacter sp. 105 MED

Sung-Yeon Joo,Hee-Wang Yoo,Sharad Sarak,Byung-Gee Kim,Hyungdon Yun

doi:10.3390/catal9010054

Sung-Yeon Joo, Hee-Wang Yoo + Show 3 more

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https://doi.org/10.3390/catal9010054

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Abstract

ω-Hydroxylated fatty acids are valuable and versatile building blocks for the production of various adhesives, lubricants, cosmetic intermediates, etc. The biosynthesis of ω-hydroxydodecanoic acid from vegetable oils is one of the important green pathways for their chemical-based synthesis. In the present study, the novel monooxygenase CYP153AL.m from Limnobacter sp. 105 MED was used for the whole-cell biotransformations. We constructed three-component system that was comprised of CYP153AL.m, putidaredoxin and putidaredoxin reductase from Pseudomonas putida. This in vivo study demonstrated that CYP153AL.m is a powerful catalyst for the biosynthesis of ω-hydroxydodecanoic acid. Under optimized conditions, the application of a solid-state powdered substrate rather than a substrate dissolved in DMSO significantly enhanced the overall reaction titer of the process. By employing this efficient system, 2 g/L of 12-hydroxydodecanoic acid (12-OHDDA) was produced from 4 g/L of its corresponding fatty acid, which was namely dodecanoic acid. Furthermore, the system was extended to produce 3.28 g/L of 12-OHDDA using 4 g/L of substrate by introducing native redox partners. These results demonstrate the utility of CYP153AL.m-catalyzed biotransformations in the industrial production of 12-OHDDA and other valuable building blocks.

Highlights

Introduction ωHydroxylated fatty acids (ω-OHFAs) obtained from medium- and long-chain length fatty acids are versatile building blocks that are used as precursors for bioplastics [1] and high-end polymers in the chemical industry [2,3]
The system was extended to produce 3.28 g/L of 12-OHDDA using 4 g/L of substrate by introducing native redox partners. These results demonstrate the utility of CYP153AL.m-catalyzed biotransformations in the industrial production of 12-OHDDA and other valuable building blocks
Introduction ω-Hydroxylated fatty acids (ω-OHFAs) obtained from medium- and long-chain length fatty acids are versatile building blocks that are used as precursors for bioplastics [1] and high-end polymers in the chemical industry [2,3]

Summary

Introduction

Introduction ωHydroxylated fatty acids (ω-OHFAs) obtained from medium- and long-chain length fatty acids are versatile building blocks that are used as precursors for bioplastics [1] and high-end polymers in the chemical industry [2,3]. To synthesize ω-OHFAs, various chemical routes have been reported, including cross-metathesis of unsaturated fatty acid esters, followed by the hydroformylation and hydrogenation of the carbonyl group [6] or by the reduction of α, ω-dicarboxylic acids [7]. The chemical-based processes for the oxidation of the unreactive carbon atom require very harsh conditions and multiple steps; depend on nonrenewable feedstocks and have poor selectivity [8]. For these reasons, attention has been focused on biological approaches. Wenhua Lu and co-workers have reported biotransformation of 200 g/L methyl tetradecanoate, which resulted into

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