Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols

Author:

Kim Hoon1ORCID,Rencoret Jorge2ORCID,Elder Thomas J.3,del Río José C.2ORCID,Ralph John14ORCID

Affiliation:

1. Department of Energy Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin-Madison, Madison, WI 53726, USA.

2. Instituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Avenida de la Reina Mercedes, 10, 41012, Seville, Spain.

3. USDA-Forest Service, Southern Research Station 521 Devall Dr. Auburn, AL 36849, USA.

4. Department of Biochemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.

Abstract

Hydroxystilbenes are a class of polyphenolic compounds that behave as lignin monomers participating in radical coupling reactions during the lignification. Here, we report the synthesis and characterization of various artificial copolymers of monolignols and hydroxystilbenes, as well as low-molecular-mass compounds, to obtain the mechanistic insights into their incorporation into the lignin polymer. Integrating the hydroxystilbenes, resveratrol and piceatannol, into monolignol polymerization in vitro, using horseradish peroxidase to generate phenolic radicals, produced synthetic lignins [dehydrogenation polymers (DHPs)]. Copolymerization of hydroxystilbenes with monolignols, especially sinapyl alcohol, by in vitro peroxidases notably improved the reactivity of monolignols and resulted in substantial yields of synthetic lignin polymers. The resulting DHPs were analyzed using two-dimensional NMR and 19 synthesized model compounds to confirm the presence of hydroxystilbene structures in the lignin polymer. The cross-coupled DHPs confirmed both resveratrol and piceatannol as authentic monomers participating in the oxidative radical coupling reactions during polymerization.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Cited by 2 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Grass lignin: biosynthesis, biological roles, and industrial applications;Frontiers in Plant Science;2024-02-23

2. Selecting Suitable Near-Native Lignins for Research;Journal of Agricultural and Food Chemistry;2023-12-08

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