Microbial assimilation of lignin-derived aromatic compounds and conversion to value-added products

Azubuike, Christopher Chibueze; Allemann, Marco N.; Michener, Joshua K.

doi:10.1016/j.mib.2021.10.014

Cited by 34 publications

(13 citation statements)

References 66 publications

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“…In lignin conversion pathways, LDFs are intermediate compounds, which need further upgradation for the production of marketable fuels and chemicals. This upgrading step can be performed by catalytic, − enzymatic, − and microbial − means with the aid of separation techniques, including solvent extraction . For all these technologies, it is important to know the solution properties of LDFs, and the solvation free energy (Δ G solv ) of a molecule in a solvent is a fundamental quantity.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory with Implicit Solvents for Accurate Estimation of Aqueous and Organic Solvation Free Energies of Lignin Fragments

Colombari

Nascimento

Liu

et al. 2022

ACS Sustainable Chem. Eng.

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Lignin is the main potential source of renewable aromatic chemicals, and solvation free energy (ΔG solv ) is a fundamental thermodynamic parameter for a compound in solution. Here, density functional theory with the electron density-based continuum solvent model (SMD-DFT) is employed to calculate ΔG solv for 283 neutral lignin depolymerization fragments and analogues (LDF&A) in water and organic solvents (1-octanol, cyclohexane, methyl-isobutyl ketone, and butyl acetate). Calculations for LDF&A are challenging due to the balance of hydrophilic oxygenations and hydrophobic aromatic rings with π orbitals. After correction of atomic van der Waals radii, calculated ΔG solv in water for a subset of 18 aromatic monomers is shown to outperform the accuracy of the FreeSolv benchmark. For organic solvents, comparisons through partition coefficients (log P) from several public datasets reveal that SMD-DFT calculations can accurately predict log P after accounting for systematic biases due to solvent admixtures not considered by the calculations. The presented results for LDF&A demonstrate that SMD-DFT provides useful estimates for log P and unprecedented accuracy for aqueous ΔG solv . The obtained datasets of aqueous and organic ΔG solv for LDF&A provide a key advancement toward accurate computer modeling of lignin processing into renewable fuels and chemicals.

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Section: Introductionmentioning

confidence: 99%

Density Functional Theory with Implicit Solvents for Accurate Estimation of Aqueous and Organic Solvation Free Energies of Lignin Fragments

Colombari

Nascimento

Liu

et al. 2022

ACS Sustainable Chem. Eng.

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“…Exploring lignin biorefineries for aromatic chemical production has promising potential to improve the lignin economic competitiveness of biomass biorefineries. According to the previous studies, many aromatic monomers from lignin can be efficiently released by pretreatment and thermochemical depolymerization [ 4 ]. These compounds mainly include various phenolic acids, such as ferulic acid, p -coumaric acid and cinnamic acid.…”

Section: Introductionmentioning

confidence: 99%

Efficient biosynthesis of pinosylvin from lignin-derived cinnamic acid by metabolic engineering of Escherichia coli

Zhang

Zou

et al. 2022

Biotechnol Biofuels

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Background The conversion of lignin-derived aromatic monomers into valuable chemicals has promising potential to improve the economic competitiveness of biomass biorefineries. Pinosylvin is an attractive pharmaceutical with multiple promising biological activities. Results Herein, Escherichia coli was engineered to convert the lignin-derived standard model monomer cinnamic acid into pinosylvin by introducing two novel enzymes from the wood plant: stilbene synthase from Pinus pinea (PpSTS) and 4-Coumarate-CoA ligase from Populus trichocarpa (Ptr4CL4). The expression of Ptr4CL4 drastically improved the production of pinosylvin (42.5 ± 1.1 mg/L), achieving values 15.7-fold higher than that of Ptr4CL5 (another 4-Coumarate-CoA ligase from Populus trichocarpa) in the absence of cerulenin. By adjusting the expression strategy, the optimized engineered strain produced pinosylvin at 153.7 ± 2.2 mg/L with an extremely high yield of 1.20 ± 0.02 mg/mg cinnamic acid in the presence of cerulenin, which is 83.9% ± 1.17 of the theoretical yield. This is the highest reported pinosylvin yield directly from cinnamic acid to date. Conclusion Our work highlights the feasibility of microbial production of pinosylvin from cinnamic acid and paves the way for converting lignin-related aromatics to valuable chemicals.

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“…5 The majority of LDACs are derived from methoxylated G and S-type subunits which must be O -demethylated to diols before they can be funnelled to high-value ring-opened compounds. 6,7 However, O -demethylation is recognised as a rate-limiting reaction limiting the conversion of LDACs to useful compounds in high atom yield. 8,9 Thus, efforts have focused on characterisation of demethylase enzymes from bacteria to improve the biological valorisation of lignin.…”

mentioning

confidence: 99%

Efficient O-demethylation of lignin monoaromatics using the peroxygenase activity of cytochrome P450 enzymes

et al. 2022

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Microbial assimilation of lignin-derived aromatic compounds and conversion to value-added products

Cited by 34 publications

References 66 publications

Density Functional Theory with Implicit Solvents for Accurate Estimation of Aqueous and Organic Solvation Free Energies of Lignin Fragments

Density Functional Theory with Implicit Solvents for Accurate Estimation of Aqueous and Organic Solvation Free Energies of Lignin Fragments

Efficient biosynthesis of pinosylvin from lignin-derived cinnamic acid by metabolic engineering of Escherichia coli

Efficient O-demethylation of lignin monoaromatics using the peroxygenase activity of cytochrome P450 enzymes

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