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Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-T_g Polymeric Materials.

ABSTRACT: As viable precursors to a diverse array of macromolecules, biomass-derived compounds must impart wide-ranging and precisely controllable properties to polymers. Herein, we report the synthesis and subsequent reversible addition-fragmentation chain-transfer polymerization of a new monomer, syringyl methacrylate (SM, 2,6-dimethoxyphenyl methacrylate), that can facilitate widespread property manipulations in macromolecules. Homopolymers and heteropolymers synthesized from SM and related monomers have broadly tunable and highly controllable glass transition temperatures ranging from 114 to 205 °C and zero-shear viscosities ranging from ?0.2 kPa·s to ?17,000 kPa·s at 220 °C, with consistent thermal stabilities. The tailorability of these properties is facilitated by the controlled polymerization kinetics of SM and the fact that one vs two o-methoxy groups negligibly affect monomer reactivity. Moreover, syringol, the precursor to SM, is an abundant component of depolymerized hardwood (e.g., oak) and graminaceous (e.g., switchgrass) lignins, making SM a potentially sustainable and low-cost candidate for tailoring macromolecular properties.

SUBMITTER: Holmberg AL

PROVIDER: S-EPMC4872261 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-<i>T</i><sub>g</sub> Polymeric Materials.

Holmberg Angela L AL Reno Kaleigh H KH Nguyen Ngoc A NA Wool Richard P RP Epps Thomas H TH

ACS macro letters 20160418 5

As viable precursors to a diverse array of macromolecules, biomass-derived compounds must impart wide-ranging and precisely controllable properties to polymers. Herein, we report the synthesis and subsequent reversible addition-fragmentation chain-transfer polymerization of a new monomer, syringyl methacrylate (SM, 2,6-dimethoxyphenyl methacrylate), that can facilitate widespread property manipulations in macromolecules. Homopolymers and heteropolymers synthesized from SM and related monomers ha ...[more]

PMID: 27213117

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Project description:New environmentally sound technologies are needed to derive valuable compounds from renewable resources. Lignin, an abundant polymer in terrestrial plants comprised predominantly of guaiacyl and syringyl monoaromatic phenylpropanoid units, is a potential natural source of aromatic compounds. In addition, the plant secondary metabolite tricin is a recently discovered and moderately abundant flavonoid in grasses. The most prevalent interunit linkage between guaiacyl, syringyl, and tricin units is the ?-ether linkage. Previous studies have shown that bacterial ?-etherase pathway enzymes catalyze glutathione-dependent cleavage of ?-ether bonds in dimeric ?-ether lignin model compounds. To date, however, it remains unclear whether the known ?-etherase enzymes are active on lignin polymers. Here we report on enzymes that catalyze ?-ether cleavage from bona fide lignin, under conditions that recycle the cosubstrates NAD+ and glutathione. Guaiacyl, syringyl, and tricin derivatives were identified as reaction products when different model compounds or lignin fractions were used as substrates. These results demonstrate an in vitro enzymatic system that can recycle cosubstrates while releasing aromatic monomers from model compounds as well as natural and engineered lignin oligomers. These findings can improve the ability to produce valuable aromatic compounds from a renewable resource like lignin.IMPORTANCE Many bacteria are predicted to contain enzymes that could convert renewable carbon sources into substitutes for compounds that are derived from petroleum. The ?-etherase pathway present in sphingomonad bacteria could cleave the abundant ?-O-4-aryl ether bonds in plant lignin, releasing a biobased source of aromatic compounds for the chemical industry. However, the activity of these enzymes on the complex aromatic oligomers found in plant lignin is unknown. Here we demonstrate biodegradation of lignin polymers using a minimal set of ?-etherase pathway enzymes, the ability to recycle needed cofactors (glutathione and NAD+) in vitro, and the release of guaiacyl, syringyl, and tricin as depolymerized products from lignin. These observations provide critical evidence for the use and future optimization of these bacterial ?-etherase pathway enzymes for industrial-level biotechnological applications designed to derive high-value monomeric aromatic compounds from lignin.

Dataset Information

Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-T_g Polymeric Materials.

Publications

Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-<i>T</i><sub>g</sub> Polymeric Materials.

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Dataset Information

Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-Tg Polymeric Materials.

Publications

Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-<i>T</i><sub>g</sub> Polymeric Materials.

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OmicsDI is part of the ELIXIR infrastructure

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Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High-T_g Polymeric Materials.