Multi-enzymatic cascade reactions with <i>Escherichia coli</i>-based modules for synthesizing various bioplastic monomers from fatty acid methyl esters

Yoo, Hee-Wang; Jung, Hyunsang; Sarak, Sharad; Kim, Ye Chan; Park, Beom Gi; Kim, Byung‐Gee; Patil, Mahesh D.; Yun, Hyungdon

doi:10.1039/d1gc04532f

Cited by 19 publications

(34 citation statements)

References 41 publications

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“…Thus, to balance its expression and activity, its integration into the genome for lower expression might be enough to achieve the required activity. In addition, since the endogenous aldo-keto reductase (AKR) responsible for aldehyde reduction in E. coli has been reported 32 , we suspected that endogenous AKR could also work for the reduction of 6-hydroxyhexanal to HDO, and the heterologous expression of AKR in E. coli could then be omitted ( Fig. 4b ).…”

Section: Resultsmentioning

confidence: 99%

Transforming inert cycloalkanes into α,ω-diamines through designed enzymatic cascade catalysis

Zhang

Fang

Wang

et al. 2022

Preprint

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Aliphatic alpha-omega-diamines (DAs) are important monomer precursors in polyamide plastic manufacturing. However, the dominant industrial process for DA synthesis involves energy-intensive, multistage chemical reactions that are harmful to the environment. For instance, 1,6-hexanediamine (HMD), one of most prominent monomers in nylon-66 synthesis, is mainly synthesized with currently high technological control by butadiene hydrocyanation, which suffers from the use of highly toxic hydrogen cyanide, unsatisfactory selectivity and a complex separation process. Thus, the development of sustainable green DA synthetic routes is highly desired. Herein, we report an efficient one-pot in vivo biocatalytic cascade for the transformation of cycloalkanes into DAs with the aid of advanced techniques, including the RetroBioCat tool for biocatalytic route design, enzyme mining for finding appropriate enzymes and microbial consortia construction for efficient pathway assembly. As a result, DAs are successfully produced by the developed microbial consortia-based biocatalytic system, especially HMD, and product concentrations as high as 16.5 mM and 7.6 mM are achieved when using cyclohexanol (CHOL) or cyclohexane (CH) as substrates, respectively. This also represents the highest HMD biosynthesis productivity to date. Other cycloalkanes also serve as substrates, indicating the generality of our approach.

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Section: Resultsmentioning

confidence: 99%

Transforming inert cycloalkanes into α,ω-diamines through designed enzymatic cascade catalysis

Zhang

Fang

Wang

et al. 2022

Preprint

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“…To the best of our knowledge, this study is the first to establish a Y. lipolytica -based biocatalytic system for the production of α,ω-diamines or ω-amino fatty acids from n -alkanes, fatty alcohols and acids. Although whole-cell catalytic systems using E. coli has been recently developed ( Yoo et al, 2022 ), the systems have the critical disadvantages including CYP expression and hydrophobic substrate uptakes. Firstly, CYP expression in E. coli requires a heme precursor, which supplements culture medium with δ-ala-leuvenic acid, an expensive commodity ( Wu et al, 2006 ; Cheesman et al, 2013 ; Ichinose and Wariishi, 2013 ; Ichinose et al, 2015 ).…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of aliphatic plastic monomers with amino residues in Yarrowia lipolytica

Park

Kim

Jang

et al. 2023

Front. Bioeng. Biotechnol.

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Introduciton: The α,ω-diamines (NH2-(CH2)n-NH2) and ω -amino fatty acids (NH2-(CH2)n-COOH) have been widely used as building blocks in polymerindustries. Medium- to long-chain (C8 to C18) fatty acid monomers with amino residues are almost exclusively produced via chemical processes that generate hazardous waste and induce severe environmental problems, such as global warming and pollution. Here, we present the construction platformstrains of Yarrowia lipolytica a cheese-ripening yeast, for direct biotransformation of hydrocarbons into medium- to long-chain α,ω-diamines and ωamino fatty acids using metabolic engineering of endogenous fatty acid ω- and β-oxidation pathways and introducing heterologous ω-transaminase in Y. lipolytica.Methods: We deleted six genes encoding the acyl-CoA oxidase (ACO1–6) and four fatty aldehyde dehydrogenase genes (FALDH1-4), which catalyze fatty acid β-oxidation and downstream oxidation of fatty aldehydes in Y. lipolytica, respectively. The ω-transaminase from Chromobacterium violaceum DSM30191 was introduced into the genome of the ΔPOX ΔFALDH strain under the control of Y. lipolytica-derived EXP1 promoters.Results and Discussion: The ΔPOX ΔFALDH strains with ω-CvTA successfully accumulated the corresponding C12 αω-diamines into a shaking culture medium with dodecane or dodecanol. In addition, these strains accumulated C12 ω-amino fatty acids from dodecanoic acid. With the commercially available α,ω-diacid bioprocess, this yeast biosynthesis producing medium- and longchain α,ω-diamines and ω-amino fatty acids could complete the yeast platform technology generating all medium- and long-chain aliphatic polyamide monomers, α,ω-biofunctionalized with one or both carboxylic acid and amino residues.

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“…Thus, to balance its expression and activity, its integration into the genome for lower expression might be enough to achieve the required activity. In addition, since the endogenous AKR responsible for aldehyde reduction in E. coli has been reported, [20] we suspected that endogenous AKR may also work for the reduction of 6-hydroxyhexanal to HDO, and the heterologous expression of AKR in E. coli could then be omitted (Figure 4b). Therefore, plasmids carrying only four enzyme genes need to be constructed for heterologous expression in E. coli, namely BVMO from Acinetobacter sp.…”

Section: Angewandte Chemiementioning

confidence: 99%

Transforming Inert Cycloalkanes into α,ω‐Diamines by Designed Enzymatic Cascade Catalysis

et al. 2023

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Aliphatic α,ω-diamines (DAs) are important monomer precursors that are industrially produced by energy-intensive, multistage chemical reactions that are harmful to the environment. Therefore, the development of sustainable green DA synthetic routes is highly desired. Herein, we report an efficient one-pot in vivo biocatalytic cascade for the transformation of cycloalkanes into DAs with the aid of advanced techniques, including the RetroBioCat tool for biocatalytic route design, enzyme mining for finding appropriate enzymes and microbial consortia construction for efficient pathway assembly. As a result, DAs were successfully produced by the designed microbial consortia-based biocatalytic system. In particular, the highest biosynthesis productivity record of 1,6-hexanediamine was achieved when using either cyclohexanol or cyclohexane as a substrate. Thus, the developed biocatalytic process provides a promising alternative to the dominant industrial process for manufacturing DAs.

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Multi-enzymatic cascade reactions with Escherichia coli-based modules for synthesizing various bioplastic monomers from fatty acid methyl esters

Abstract: Multi-enzymatic cascade reaction systems were designed to generate biopolymer monomers using Escherichia coli-based cell modules, capable of carrying out one-pot reactions. Three cell-based modules, including a ω-hydroxylation module (Cell-Hm) to...

Cited by 19 publications

References 41 publications

Transforming inert cycloalkanes into α,ω-diamines through designed enzymatic cascade catalysis

Transforming inert cycloalkanes into α,ω-diamines through designed enzymatic cascade catalysis

Biosynthesis of aliphatic plastic monomers with amino residues in Yarrowia lipolytica

Transforming Inert Cycloalkanes into α,ω‐Diamines by Designed Enzymatic Cascade Catalysis

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