One-Pot Synthesis of Adipic Acid from Guaiacol in <i>Escherichia coli</i>

Suitor, Jack T.; Varzandeh, Simon; Wallace, Stephen

doi:10.1021/acssynbio.0c00254

Cited by 26 publications

(23 citation statements)

References 18 publications

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“…It has been the subject of theoretical investigation 29 and has recently been successfully deployed in an engineered E. coli strain for the production of adipic acid. 30 …”

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confidence: 99%

Engineering a Cytochrome P450 for Demethylation of Lignin-Derived Aromatic Aldehydes

Ellis

Hinchen

Bleem

et al. 2021

JACS Au

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Biological funneling of lignin-derived aromatic compounds is a promising approach for valorizing its catalytic depolymerization products. Industrial processes for aromatic bioconversion will require efficient enzymes for key reactions, including demethylation of O -methoxy-aryl groups, an essential and often rate-limiting step. The recently characterized GcoAB cytochrome P450 system comprises a coupled monoxygenase (GcoA) and reductase (GcoB) that catalyzes oxidative demethylation of the O- methoxy-aryl group in guaiacol. Here, we evaluate a series of engineered GcoA variants for their ability to demethylate o -and p -vanillin, which are abundant lignin depolymerization products. Two rationally designed, single amino acid substitutions, F169S and T296S, are required to convert GcoA into an efficient catalyst toward the o - and p -isomers of vanillin, respectively. Gain-of-function in each case is explained in light of an extensive series of enzyme-ligand structures, kinetic data, and molecular dynamics simulations. Using strains of Pseudomonas putida KT2440 already optimized for p -vanillin production from ferulate, we demonstrate demethylation by the T296S variant in vivo . This work expands the known aromatic O- demethylation capacity of cytochrome P450 enzymes toward important lignin-derived aromatic monomers.

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“…It has been the subject of theoretical investigation 29 and has recently been successfully deployed in an engineered E. coli strain for the production of adipic acid. 30 …”

mentioning

confidence: 99%

Engineering a Cytochrome P450 for Demethylation of Lignin-Derived Aromatic Aldehydes

Ellis

Hinchen

Bleem

et al. 2021

JACS Au

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“…Guaiacol, one of the central elements of softwood lignin, is a promising natural resource with great application and significance in industrial production. [127] Very recently, Kosuke and coworkers successfully prepared AA from bio-based guaiacol through the intermediate of 2-methoxycyclohexanone (2-MCO) by aerobic oxidation using phosphotungstic acid (H 3 PW 12 O 40 ) catalyst. [128] For the first step, Pd-based catalysts have been shown to be effective in selective hydrogenation of phenolic compounds and the conversion of guaiacol to 2-MCO over Pd/ HAP catalyst has been actually reported with 98 % high selectivity.…”

Section: Preparation Of Adipic Acid From Guaiacol and Catecholmentioning

confidence: 99%

“…Recently, Suitor and co-workers conducted the pioneering work of a one-pot preparation of AA from guaiacol and catechol using genetically engineered Escherichia coli cells. [127] The reaction process is mild, requires no other additives and produces no by-products. The authors firstly established an expression vector that contains the catA and BcER genes from Amycolatopsis sp.…”

Section: Preparation Of Adipic Acid From Guaiacol and Catecholmentioning

confidence: 99%

Sustainable Routes for the Synthesis of Renewable Adipic Acid from Biomass Derivatives

Lang

2021

ChemSusChem

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Adipic acid (AA) is a key industrial dicarboxylic acid intermediate used in nylon manufacturing. Unfortunately, the traditional process technology is accompanied by serious environmental pollution. Given the growing demand for adipic acid and the desire to reduce its negative impact on the environment, considerable efforts have been devoted to developing more green and friendly routes. This Review is focused on the latest advances in the sustainable preparation of AA from biomassbased platform molecules, including 5-hydroxymethylfufural, glucose, γ-valerolactone, and phenolic compounds, through biocatalysis, chemocatalysis, and the combination of both.Additionally, the development of state-of-the-art catalysts for different catalytic systems systematically is discussed and summarized, as well as their reaction mechanisms. Finally, the prospects for all preparation routes are critically evaluated and key technical challenges in the development of green and sustainable processes for the manufacture of AA are highlighted. It is hoped that the green adipic acid synthesis pathways presented can provide insights and guidance for further research into other industrial processes for the production of nylon precursors in the future.

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“…Suitor et al. [ 66 ] described the first synthesis of adipic acid from guaiacol, a lignin‐derived feedstock, in the biotechnology industry workhorse bacterium Escherichia coli . Effectively, lignin is a waste, and its conversion to adipic acid using synthetic biology keeps it in circulation, thereby contributing both to the bioeconomy and the circular economy.…”

Section: Engineering Biology Is Highly Disruptive Technologymentioning

confidence: 99%

Addressing the post‐COVID era through engineering biology

Bell

Philp

Kitney

2021

Engineering Biology

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Currently, the world is faced with two fundamental issues of great importance, namely climate change and the coronavirus pandemic. These are intimately involved with the need to control climate change and the need to switch from high carbon, unsustainable economies to low carbon economies. Inherent in this approach are the concepts of the bioeconomy and the Green Industrial Revolution. The article addresses both issues, but it, principally, focusses on the development of the bioeconomy. It considers how nations are divided in relation to the use of biotechnology and synthetic biology in terms of their bioeconomy strategies. The article addresses, as a central theme, the nature and role of engineering biology in these developments. Engineering biology is addressed in terms of BioDesign, coupled with high levels of automation (including AI and machine learning) to increase reproducibility and reliability to meet industrial standards. This lends itself to distributed manufacturing of products in a range of fields. Engineering biology is a platform technology that can be applied in a range of sectors. The bioeconomy, as an engine for economic growth is addressed—in terms of moving from oil‐based economies to bio‐based economies—using biomass, for example, using selected lignocellulosic waste as a feedstock.

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One-Pot Synthesis of Adipic Acid from Guaiacol in Escherichia coli

Cited by 26 publications

References 18 publications

Engineering a Cytochrome P450 for Demethylation of Lignin-Derived Aromatic Aldehydes

Engineering a Cytochrome P450 for Demethylation of Lignin-Derived Aromatic Aldehydes

Sustainable Routes for the Synthesis of Renewable Adipic Acid from Biomass Derivatives

Addressing the post‐COVID era through engineering biology

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