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

Md Ahsan,Hyunwoo Jeon,Mahesh Patil,Taeowan Chung,Sihyong Sung,Hyungdon Yun

doi:10.3390/catal8010004

Md Ahsan, Hyunwoo Jeon + Show 4 more

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https://doi.org/10.3390/catal8010004

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Abstract

α,ω-Diols are important monomers widely used for the production of polyesters and polyurethanes. Here, biosynthesis of α,ω-diols (C8–C16) 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.

Highlights

The utilization of renewable feedstock-derived raw materials and development of bioprocesses thereof to substitute petroleum-based products in polymer industry has shown a steep surge in recent years [1,2,3] due to concern of future shortage of petroleum resources and in consideration of green production [4,5]
Biocatalysis has countless advantages including high efficiency, increased stability, high degree of selectivity, and safe reaction conditions [6,7]. α,ω-Diols are used as monomers for the production of polyesters and polyurethanes [1,2]
Industrial-scale preparation has only been confined to short-chain diol biosynthesis, while biosynthesis of medium- to long-chain α,ω-diols (C8 –C16 ) has not been studied extensively [8,9]

Summary

Introduction

The utilization of renewable feedstock-derived raw materials and development of bioprocesses thereof to substitute petroleum-based products in polymer industry has shown a steep surge in recent years [1,2,3] due to concern of future shortage of petroleum resources and in consideration of green production [4,5]. Industrial-scale preparation has only been confined to short-chain diol biosynthesis, while biosynthesis of medium- to long-chain α,ω-diols (C8 –C16 ) has not been studied extensively [8,9]. Microbial synthesis of α,ω-diol (>C12 ) has been originally reported in some yeasts species belonging to genus Candida [10,11,12]. Further microbial synthesis α,ω-diols (C5 –C12 ) from alkanes employing cytochrome P450 (CYP5153A) from Acinetobacter sp. OC4 in Escherichia coli with the highest yielded for 1,8-octanediol (722 mg/L) has been reported [10,13]

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