Chemoenzymatic valorization of agricultural wastes into 4-hydroxyvaleric acid via levulinic acid

Moon, Myounghoon; Yeon, Young Joo; Park, Hyun June; Park, Jisu; Park, Gwon Woo; Kim, Gil-Hwan; Lee, Joon-Pyo; Lee, Jun Young; Lee, Jin-Suk; Min, Kyoungseon

doi:10.1016/j.biortech.2021.125479

Cited by 25 publications

(10 citation statements)

References 21 publications

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“…4-HV is an industrially relevant monomer of biodegradable polymers and a precursor of γ-valerolactone, which is used as a fuel, solvent, food additive, and precursor for value-added carbon chemicals ( Gorenflo et al, 2001 ; Bond et al, 2010 ; Yan et al, 2015 ). In addition to the chemical synthesis of 4-HV, 50–100 g/L of 4-HV has been biologically produced using novel pathways and engineered microbial strains ( Kim D. et al, 2019 ; Sathesh-Prabu and Lee, 2019 ; Moon et al, 2021 ). Notably, these production systems require dedicated plasmids, antibiotics, and expensive inducers to generate multiple gene copies, select and retain the plasmid, and efficiently induce the expression of synthetic pathway genes.…”

Section: Discussionmentioning

confidence: 99%

“…In addition, the co-substrate, formate, is produced during the conversion of cellulosic hexose sugars to LA. Equimolar production of LA and formate was obtained from cellulosic biomass such as corn cob and rice straw ( Moon et al, 2021 ). Therefore, the presented system could be useful to produce LA-derived chemicals under the LA-inducible expression system.…”

Section: Discussionmentioning

confidence: 99%

“…The conventional chemical synthesis of 4-HV as an intermediate or via the depolymerization of intracellularly produced PHA has various shortcomings, including low yield, the use of harsh conditions, metal catalysts, and organic solvents, the need for chemical modification, and incomplete depolymerization ( Martin and Prather, 2009 ). 4-HV can be produced from levulinic acid (LA) ( Martin and Prather, 2009 ; Yeon et al, 2013 ; Sathesh-Prabu and Lee, 2019 ; Moon et al, 2021 ). We previously engineered the lva operon involved in LA catabolism in Pseudomonas putida KT2440 ( Rand et al, 2017 ) and produced 50 g/L of 4-HV by overexpressing the heterologous acyl-CoA thioesterase gene, tesB , under the LA-inducible LvaR/P lvaA expression system, with a molar conversion of 97% from LA in shake-flask cultures ( Sathesh-Prabu and Lee, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

“…putida KT2440 ( Sathesh-Prabu et al, 2021b ) and Methylorubrum extorquens AM1 strains ( Sathesh-Prabu et al, 2021a ). LA is a sustainable molecule that can be obtained from renewable cellulosic biomass via acid-catalyzed dehydration and hydrolysis ( Hayes and Becer, 2020 ; Moon et al, 2021 ). Substrate-inducible expression systems have attracted attention for the microbial synthesis of biochemicals, as they do not require expensive chemical inducers.…”

Section: Introductionmentioning

confidence: 99%

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Substrate-inducible and antibiotic-free high-level 4-hydroxyvaleric acid production in engineered Escherichia coli

Sathesh‐Prabu

Tiwari

Lee

2022

Front. Bioeng. Biotechnol.

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In this study, we developed a levulinic acid (LA)-inducible and antibiotic-free plasmid system mediated by HpdR/PhpdH and infA-complementation to produce 4-hydroxyvaleric acid (4-HV) from LA in an engineered Escherichia coli strain. The system was efficiently induced by the addition of the LA substrate and resulted in tight dose-dependent control and fine-tuning of gene expression. By engineering the 5′ untranslated region (UTR) of hpdR mRNA, the gene expression of green fluorescent protein (GFP) increased by at least two-fold under the hpdH promoter. Furthermore, by evaluating the robustness and plasmid stability of the proposed system, the engineered strain, IRV750f, expressing the engineered 3-hydroxybutyrate dehydrogenase (3HBDH∗) and formate dehydrogenase (CbFDH), produced 82 g/L of 4-HV from LA, with a productivity of 3.4 g/L/h and molar conversion of 92% in the fed-batch cultivation (5 L fermenter) without the addition of antibiotics or external inducers. Overall, the reported system was highly beneficial for the large-scale and cost-effective microbial production of value-added products and bulk chemicals from the renewable substrate, LA.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Substrate-inducible and antibiotic-free high-level 4-hydroxyvaleric acid production in engineered Escherichia coli

Sathesh‐Prabu

Tiwari

Lee

2022

Front. Bioeng. Biotechnol.

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“…In recent years, enzymatic synthesis of polyol esters has attracted more and more attention due to its mild reaction conditions, environmental friendliness and fewer by-products (Mukherjee et al, 2015;Jaiswal and Rathod, 2021). The application of lipase in enzymatic esteri cation reaction has been developed signi cantly, and the immobilized lipase has signi cantly improved the catalytic activity and stability of the enzyme (Moon et al, 2021;Song et al, 2021).The addition of organic solvents provides many bene ts for enzymecatalyzed reactions (Zhu et al, 2020). However, using organic solvents requires expensive reactors and tools, leading to their limited use in industry.…”

Section: Introductionmentioning

confidence: 99%

Enzyme-catalyzed Synthesis of Novel Solid–liquid Phase Change Energy Storage Materials Based on Levulinic Acid and 1,4 butanediol

Zhai

Zhao

et al. 2021

Preprint

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With the rapid development of society, all kinds of non-renewable energy resources are constantly developed and utilized, energy storage is one of the best ways to solve the energy shortage. In this study , levulinic acid (LA) and 1,4 butanediol (BDO) were used to synthesize a novel polyol ester (LABDO) by biological and chemical methods. The biological method exhibited excellent performance in the synthesis process, where 87.5% of LABDO yield under optimal conditions, while the chemical method had more byproducts and higher energy consumption. Finally, the thermal properties of the obtained phase change materials (PCMs) were evaluated. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) showed that the melting temperature of LABDO was 50.51°C, the latent heat of melting was 156.1J/g, and the pyrolysis temperature was 150-160°C. Compared with traditional paraffin wax, the prepared PCMs have suitable phase transition temperature, higher latent heat of melting and better thermal stability. The thermal conductivity can be increased to 0.34W·m-1· k-1 by adding expanded graphite. In summary, LABDO can be used as low temperature phase change energy storage materials.

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Stereoselective Synthesis of γ‐(Acyloxy)carboxylic Acids and γ‐Lactones Featuring the Switch of Stereopreference of Candida antarctica Lipase B in Sodium γ‐Hydroxycarboxylate Homologues

et al. 2022

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Scalable protocols of straightforward synthesis of enantiomeric γ‐(acyloxy)carboxylic acids and γ‐lactones are presented. The key step is lipase‐catalyzed stereoselective acylation of γ‐hydroxycarboxylic acid sodium salt in organic solvent followed by acidification of the product, extraction and acidic relactonization of the unreacted enantiomer. The mixture of γ‐(acyloxy)carboxylic acid and γ‐lactone is separated either by extraction with solution of sodium bicarbonate or by distillation. A switch of enantioinduction of Candida antarctica lipase B along homologous nucleophiles from R configuration of γ‐hydroxyhexanoic acid salt to S configuration of the C7 and longer‐chain homologues has been disclosed. Both enantiomers of γ‐(acyloxy)pentanoic acids; γ‐(acetyloxy)octanoic and ‐nonanoic acids with S configuration; [(1S,5R)‐5‐(chloroacetyloxy)cyclopent‐2‐en‐1‐yl]acetic acid and enantiomeric γ‐lactones derived from them were prepared with e. r. >98.5/1.5. The rates of acylation of C5 to C9 homologous salts differ by three orders of magnitude but remain applicable for preparative synthesis by variation of the enzyme loading and reaction time.

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Chemoenzymatic valorization of agricultural wastes into 4-hydroxyvaleric acid via levulinic acid

Cited by 25 publications

References 21 publications

Substrate-inducible and antibiotic-free high-level 4-hydroxyvaleric acid production in engineered Escherichia coli

Substrate-inducible and antibiotic-free high-level 4-hydroxyvaleric acid production in engineered Escherichia coli

Enzyme-catalyzed Synthesis of Novel Solid–liquid Phase Change Energy Storage Materials Based on Levulinic Acid and 1,4 butanediol

Stereoselective Synthesis of γ‐(Acyloxy)carboxylic Acids and γ‐Lactones Featuring the Switch of Stereopreference of Candida antarctica Lipase B in Sodium γ‐Hydroxycarboxylate Homologues

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