Incorporation of catechyl monomers into lignins: lignification from the non-phenolic end via Diels–Alder cycloaddition?

Ando, Daisuke; Lu, Fachuang; Kim, Hoon; Eugene, Alexis; Tobimatsu, Yuki; Vanholme, Ruben; Elder, Thomas J.; Boerjan, Wout; Ralph, John

doi:10.1039/D1GC03022A

Title: Incorporation of catechyl monomers into lignins: lignification from the non-phenolic end via Diels–Alder cycloaddition?

Journal Article · Tue Nov 16 00:00:00 EST 2021 · Green Chemistry

DOI:https://doi.org/10.1039/D1GC03022A· OSTI ID:1827486

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Department of Energy, Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, Madison, Wisconsin 53726, USA
Department of Energy, Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, Madison, Wisconsin 53726, USA, State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, 381 Wushan Rd, Tianhe District, Guangzhou, 510640, P.R. China
Research Institute for Sustainable Humanosphere, Kyoto University, Gokasho, Uji, 611-0011, Japan
Department of Plant Biotechnology and Bioinformatics, Ghent University, B-9052 Gent, Belgium, Center for Plant Systems Biology, VIB, B-9052 Gent, Belgium
USDA-Forest Service, Southern Research Station, 521 Devall Drive, Auburn, AL 36849, USA
Department of Energy, Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, Madison, Wisconsin 53726, USA, Department of Biochemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA, Department of Biological System Engineering, University of Wisconsin-Madison, Madison, Wisconsin 53726, USA

Canonical lignification occurs via the coupling of phenolic radicals, in which chain extension can occur only from phenolic ends of growing polymer chains. Radical coupling of catechyl monomers, including caffeyl and 5-hydroxyconiferyl alcohols, gives rise to benzodioxane units in the polymer. Anticipating that a catechol could oxidize to its o-benzoquinone analog under the dehydrogenative (oxidative) conditions of lignification, we examined the possibility that an o-benzoquinone, as the diene component, could also incorporate into lignin via another mechanism, the Diels–Alder cycloaddition reaction. The o-benzoquinone derived from methyl 5-hydroxyvanillate and 4-O-methylconiferyl alcohol served as models for the diene and dienophile, respectively, and produced Diels–Alder products in vitro. Two types of Diels–Alder products were found: (i) when the 1,2-diketone of the quinone acts as the diene in a hetero-Diels–Alder reaction, a benzodioxane structure was produced with a different regiochemistry than the benzodioxane isomer produced via radical coupling; (ii) when the quinone's diene participated in the Diels–Alder reaction, a distinctive oxatricyclo structure was produced. Both features may be used as markers for the occurrence of Diels–Alder reactions in lignification. Examination of natural lignins derived from catechyl monomers, however, did not reveal evidence for such products. The conclusion is that the only significant reactions in lignification are combinatorial radical coupling reactions of the single-electron-oxidized phenolics and that polymer chain extension therefore occurs only from the phenolic end-units even in the special case of plants that utilize catechyl monomers for lignification.

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Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0018409

OSTI ID:: 1827486

Alternate ID(s):: OSTI ID: 1978794

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Vol. 23 Journal Issue: 22; ISSN 1463-9262

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Title: Incorporation of catechyl monomers into lignins: lignification from the non-phenolic end via Diels–Alder cycloaddition?

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