Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification

Yue, Fengxia; Lu, Fachuang; Regner, Matt; Sun, Runcang; Ralph, John

doi:10.1002/cssc.201700101

Title: Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification

Journal Article · 26 January 2017 · ChemSusChem

DOI: https://doi.org/10.1002/cssc.201700101 · OSTI ID:1346254

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South China University of Technology, Tianhe District, Guangzhou (China). State Key Laboratory of Pulp and Paper Engineering; Univ. of Wisconsin, Madison, WI (United States). Department of Biochemistry and DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute
Univ. of Wisconsin, Madison, WI (United States). Department of Biochemistry and DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute
Beijing Forestry University, Haidian District, Beijing (China). Beijing Key Laboratory of Lignocellulosic Chemistry

Lignin structural studies play an essential role both in understanding the development of plant cell walls and for valorizing lignocellulosics as renewable biomaterials. Dimeric products released by selectively cleaving β–aryl ether linkages between lignin units reflect the distribution of recalcitrant lignin units, but have been neither absolutely defined nor quantitatively determined. Here in this work, 12 guaiacyl-type thioacidolysis dimers were identified and quantified using newly synthesized standards. One product previously attributed to deriving from β–1-coupled units was established as resulting from β–5 units, correcting an analytical quandary. Another longstanding dilemma, that no β–β dimers were recognized in thioacidolysis products from gymnosperms, was resolved with the discovery of two such authenticated compounds. Finally, individual GC response factors for each standard compound allowed rigorous quantification of dimeric products released from softwood lignins, affording insight into the various interunit-linkage distributions in lignins and thereby guiding the valorization of lignocellulosics.

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

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: FC02-07ER64494; FC02- 07ER64494

OSTI ID:: 1346254

Alternate ID(s):: OSTI ID: 1346255; OSTI ID: 1427629

Journal Information:: ChemSusChem, Vol. 10, Issue 5; ISSN 1864-5631

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 37 works

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Abundance and Reactivity of Dibenzodioxocins in Softwood Lignin Argyropoulos, Dimitris S.; Jurasek, Lubo; Krištofová, Lívia Journal of Agricultural and Food Chemistry, Vol. 50, Issue 4 https://doi.org/10.1021/jf010909g	journal	February 2002
Syntheses of Lignin-Derived Thioacidolysis Monomers and Their Uses as Quantitation Standards Yue, Fengxia; Lu, Fachuang; Sun, Run-Cang Journal of Agricultural and Food Chemistry, Vol. 60, Issue 4 https://doi.org/10.1021/jf204481x	journal	January 2012
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Recent Advances in Understanding Lignin Biosynthesis Whetten, Ross W.; MacKay, John J.; Sederoff, Ronald R. Annual Review of Plant Physiology and Plant Molecular Biology, Vol. 49, Issue 1 https://doi.org/10.1146/annurev.arplant.49.1.585	journal	June 1998

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Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields Anderson, Eric M.; Stone, Michael L.; Katahira, Rui Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09986-1	journal	May 2019
Structural characteristics of lignin in pruning residues of olive tree (Olea europaea L.) Rencoret, Jorge; Gutiérrez, Ana; Castro, Eulogio Holzforschung, Vol. 73, Issue 1 https://doi.org/10.1515/hf-2018-0077	journal	December 2018
Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields Anderson, Eric M.; Stone, Michael L.; Katahira, Rui Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09986-1	journal	May 2019

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Title: Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification

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