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

Abstract

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.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [2]
  1. State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, 381 Wushan Rd Tianhe District Guangzhou 510640 P. R. China, Department of Biochemistry and DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin-Madison, 1552 University Ave. Madison WI 53726 USA
  2. Department of Biochemistry and DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin-Madison, 1552 University Ave. Madison WI 53726 USA
  3. Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, 35 Qinghua East Rd Haidian District Beijing 100083 P. R. China
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1346254
Alternate Identifier(s):
OSTI ID: 1346255; OSTI ID: 1427629
Grant/Contract Number:  
FC02- 07ER64494; FC02-07ER64494
Resource Type:
Published Article
Journal Name:
ChemSusChem
Additional Journal Information:
Journal Name: ChemSusChem Journal Volume: 10 Journal Issue: 5; Journal ID: ISSN 1864-5631
Publisher:
ChemPubSoc Europe
Country of Publication:
Germany
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; analytical methods; GC-FID; lignin dimers; response factor; synthesis design

Citation Formats

Yue, Fengxia, Lu, Fachuang, Regner, Matt, Sun, Runcang, and Ralph, John. Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification. Germany: N. p., 2017. Web. doi:10.1002/cssc.201700101.
Yue, Fengxia, Lu, Fachuang, Regner, Matt, Sun, Runcang, & Ralph, John. Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification. Germany. doi:10.1002/cssc.201700101.
Yue, Fengxia, Lu, Fachuang, Regner, Matt, Sun, Runcang, and Ralph, John. Wed . "Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification". Germany. doi:10.1002/cssc.201700101.
@article{osti_1346254,
title = {Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification},
author = {Yue, Fengxia and Lu, Fachuang and Regner, Matt and Sun, Runcang and Ralph, John},
abstractNote = {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.},
doi = {10.1002/cssc.201700101},
journal = {ChemSusChem},
number = 5,
volume = 10,
place = {Germany},
year = {2017},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/cssc.201700101

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Cited by: 3 works
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