Nucleophilic Thiols Reductively Cleave Ether Linkages in Lignin Model Polymers and Lignin.
Identifieur interne : 000246 ( Main/Exploration ); précédent : 000245; suivant : 000247Nucleophilic Thiols Reductively Cleave Ether Linkages in Lignin Model Polymers and Lignin.
Auteurs : Grace E. Klinger [États-Unis] ; Yuting Zhou [États-Unis] ; Juliet A. Foote [États-Unis] ; Abby M. Wester [États-Unis] ; Yanbin Cui [États-Unis] ; Manar Alherech [États-Unis] ; Shannon S. Stahl [États-Unis] ; James E. Jackson [États-Unis] ; Eric L. Hegg [États-Unis]Source :
- ChemSusChem [ 1864-564X ] ; 2020.
Abstract
Lignin may serve as a renewable feedstock for the production of chemicals and fuels if mild, scalable processes for its depolymerization can be devised. The use of small organic thiols represents a bioinspired strategy to cleave the β-O-4 bond, the most common linkage in lignin. In the present study, synthetic β-O-4 linked polymers were treated with organic thiols, yielding up to 90 % cleaved monomer products. Lignin extracted from poplar was also treated with organic thiols resulting in molecular weight reductions as high as 65 % (Mn ) in oxidized lignin. Thiol-based cleavage of other lignin linkages was also explored in small-molecule model systems to uncover additional potential pathways by which thiols might depolymerize lignin. The success of thiol-mediated cleavage on model dimers, polymers, and biomass-derived lignin illustrates the potential utility of small redox-active molecules to penetrate complex polymer matrices for depolymerization and subsequent valorization of lignin into fuels and chemicals.
DOI: 10.1002/cssc.202001238
PubMed: 32668064
PubMed Central: PMC7540407
Affiliations:
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Klinger</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation><affiliation wicri:level="4"><nlm:affiliation>Department of Biochemistry & Molecular Biology, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Biochemistry & Molecular Biology, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation><affiliation wicri:level="4"><nlm:affiliation>DOE Great Lakes Bioenergy Research Center, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>DOE Great Lakes Bioenergy Research Center, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation></author><author><name sortKey="Zhou, Yuting" sort="Zhou, Yuting" uniqKey="Zhou Y" first="Yuting" last="Zhou">Yuting Zhou</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation></author><author><name sortKey="Foote, Juliet A" sort="Foote, Juliet A" uniqKey="Foote J" first="Juliet A" last="Foote">Juliet A. Foote</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation></author><author><name sortKey="Wester, Abby M" sort="Wester, Abby M" uniqKey="Wester A" first="Abby M" last="Wester">Abby M. Wester</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation></author><author><name sortKey="Cui, Yanbin" sort="Cui, Yanbin" uniqKey="Cui Y" first="Yanbin" last="Cui">Yanbin Cui</name><affiliation wicri:level="2"><nlm:affiliation>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706</wicri:regionArea><placeName><region type="state">Wisconsin</region></placeName></affiliation><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706</wicri:regionArea><wicri:noRegion>53706</wicri:noRegion></affiliation></author><author><name sortKey="Alherech, Manar" sort="Alherech, Manar" uniqKey="Alherech M" first="Manar" last="Alherech">Manar Alherech</name><affiliation wicri:level="2"><nlm:affiliation>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706</wicri:regionArea><placeName><region type="state">Wisconsin</region></placeName></affiliation><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706</wicri:regionArea><wicri:noRegion>53706</wicri:noRegion></affiliation></author><author><name sortKey="Stahl, Shannon S" sort="Stahl, Shannon S" uniqKey="Stahl S" first="Shannon S" last="Stahl">Shannon S. Stahl</name><affiliation wicri:level="2"><nlm:affiliation>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706</wicri:regionArea><placeName><region type="state">Wisconsin</region></placeName></affiliation><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706</wicri:regionArea><wicri:noRegion>53706</wicri:noRegion></affiliation></author><author><name sortKey="Jackson, James E" sort="Jackson, James E" uniqKey="Jackson J" first="James E" last="Jackson">James E. Jackson</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation></author><author><name sortKey="Hegg, Eric L" sort="Hegg, Eric L" uniqKey="Hegg E" first="Eric L" last="Hegg">Eric L. Hegg</name><affiliation wicri:level="4"><nlm:affiliation>Department of Biochemistry & Molecular Biology, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Biochemistry & Molecular Biology, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation><affiliation wicri:level="4"><nlm:affiliation>DOE Great Lakes Bioenergy Research Center, Michigan State University, East Lansing, MI, 48824, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>DOE Great Lakes Bioenergy Research Center, Michigan State University, East Lansing, MI, 48824</wicri:regionArea><orgName type="university">Université d'État du Michigan</orgName><placeName><settlement type="city">East Lansing</settlement><region type="state">Michigan</region></placeName></affiliation></author></analytic><series><title level="j">ChemSusChem</title><idno type="eISSN">1864-564X</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Lignin may serve as a renewable feedstock for the production of chemicals and fuels if mild, scalable processes for its depolymerization can be devised. The use of small organic thiols represents a bioinspired strategy to cleave the β-O-4 bond, the most common linkage in lignin. In the present study, synthetic β-O-4 linked polymers were treated with organic thiols, yielding up to 90 % cleaved monomer products. Lignin extracted from poplar was also treated with organic thiols resulting in molecular weight reductions as high as 65 % (M<sub>n</sub> ) in oxidized lignin. Thiol-based cleavage of other lignin linkages was also explored in small-molecule model systems to uncover additional potential pathways by which thiols might depolymerize lignin. The success of thiol-mediated cleavage on model dimers, polymers, and biomass-derived lignin illustrates the potential utility of small redox-active molecules to penetrate complex polymer matrices for depolymerization and subsequent valorization of lignin into fuels and chemicals.</div></front></TEI><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">32668064</PMID><DateRevised><Year>2020</Year><Month>10</Month><Day>10</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1864-564X</ISSN><JournalIssue CitedMedium="Internet"><PubDate><Year>2020</Year><Month>Jul</Month><Day>15</Day></PubDate></JournalIssue><Title>ChemSusChem</Title><ISOAbbreviation>ChemSusChem</ISOAbbreviation></Journal><ArticleTitle>Nucleophilic Thiols Reductively Cleave Ether Linkages in Lignin Model Polymers and Lignin.</ArticleTitle><ELocationID EIdType="doi" ValidYN="Y">10.1002/cssc.202001238</ELocationID><Abstract><AbstractText>Lignin may serve as a renewable feedstock for the production of chemicals and fuels if mild, scalable processes for its depolymerization can be devised. The use of small organic thiols represents a bioinspired strategy to cleave the β-O-4 bond, the most common linkage in lignin. In the present study, synthetic β-O-4 linked polymers were treated with organic thiols, yielding up to 90 % cleaved monomer products. Lignin extracted from poplar was also treated with organic thiols resulting in molecular weight reductions as high as 65 % (M<sub>n</sub> ) in oxidized lignin. Thiol-based cleavage of other lignin linkages was also explored in small-molecule model systems to uncover additional potential pathways by which thiols might depolymerize lignin. The success of thiol-mediated cleavage on model dimers, polymers, and biomass-derived lignin illustrates the potential utility of small redox-active molecules to penetrate complex polymer matrices for depolymerization and subsequent valorization of lignin into fuels and chemicals.</AbstractText><CopyrightInformation>© 2020 The Authors. Published by Wiley-VCH GmbH.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Klinger</LastName><ForeName>Grace E</ForeName><Initials>GE</Initials><Identifier Source="ORCID">http://orcid.org/0000-0001-8539-0412</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Biochemistry & Molecular Biology, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>DOE Great Lakes Bioenergy Research Center, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhou</LastName><ForeName>Yuting</ForeName><Initials>Y</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-8751-9686</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Foote</LastName><ForeName>Juliet A</ForeName><Initials>JA</Initials><AffiliationInfo><Affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wester</LastName><ForeName>Abby M</ForeName><Initials>AM</Initials><AffiliationInfo><Affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cui</LastName><ForeName>Yanbin</ForeName><Initials>Y</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-0708-1029</Identifier><AffiliationInfo><Affiliation>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Alherech</LastName><ForeName>Manar</ForeName><Initials>M</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-9913-5647</Identifier><AffiliationInfo><Affiliation>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Stahl</LastName><ForeName>Shannon S</ForeName><Initials>SS</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-9000-7665</Identifier><AffiliationInfo><Affiliation>DOE Great Lakes Bioenergy Research Center, University of Wisconsin-Madison, Madison, WI 53706, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Chemistry, University of Wisconsin-Madison, Madison, WI, 53706, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Jackson</LastName><ForeName>James E</ForeName><Initials>JE</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-4506-7415</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hegg</LastName><ForeName>Eric L</ForeName><Initials>EL</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-2055-5495</Identifier><AffiliationInfo><Affiliation>Department of Biochemistry & Molecular Biology, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>DOE Great Lakes Bioenergy Research Center, Michigan State University, East Lansing, MI, 48824, USA.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>DE-SC0018409</GrantID><Agency>Great Lakes Bioenergy Research Center, U.S. Department of Energy, Office of Science, Office of Biological and Environmental Research</Agency><Country></Country></Grant><Grant><GrantID>DE-FC02-07ER64494</GrantID><Agency>Great Lakes Bioenergy Research Center, U.S. Department of Energy, Office of Science, Office of Biological and Environmental Research</Agency><Country></Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>07</Month><Day>15</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>ChemSusChem</MedlineTA><NlmUniqueID>101319536</NlmUniqueID><ISSNLinking>1864-5631</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">ether</Keyword><Keyword MajorTopicYN="N">homogeneous catalysis</Keyword><Keyword MajorTopicYN="N">lignin</Keyword><Keyword MajorTopicYN="N">polymers</Keyword><Keyword MajorTopicYN="N">sulfur</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>05</Month><Day>15</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>07</Month><Day>11</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>7</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>7</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>7</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>aheadofprint</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32668064</ArticleId><ArticleId IdType="doi">10.1002/cssc.202001238</ArticleId><ArticleId IdType="pmc">PMC7540407</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>J Biol 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Michigan</li></orgName></list><tree><country name="États-Unis"><region name="Michigan"><name sortKey="Klinger, Grace E" sort="Klinger, Grace E" uniqKey="Klinger G" first="Grace E" last="Klinger">Grace E. Klinger</name></region><name sortKey="Alherech, Manar" sort="Alherech, Manar" uniqKey="Alherech M" first="Manar" last="Alherech">Manar Alherech</name><name sortKey="Alherech, Manar" sort="Alherech, Manar" uniqKey="Alherech M" first="Manar" last="Alherech">Manar Alherech</name><name sortKey="Cui, Yanbin" sort="Cui, Yanbin" uniqKey="Cui Y" first="Yanbin" last="Cui">Yanbin Cui</name><name sortKey="Cui, Yanbin" sort="Cui, Yanbin" uniqKey="Cui Y" first="Yanbin" last="Cui">Yanbin Cui</name><name sortKey="Foote, Juliet A" sort="Foote, Juliet A" uniqKey="Foote J" first="Juliet A" last="Foote">Juliet A. Foote</name><name sortKey="Hegg, Eric L" sort="Hegg, Eric L" uniqKey="Hegg E" first="Eric L" last="Hegg">Eric L. Hegg</name><name sortKey="Hegg, Eric L" sort="Hegg, Eric L" uniqKey="Hegg E" first="Eric L" last="Hegg">Eric L. Hegg</name><name sortKey="Jackson, James E" sort="Jackson, James E" uniqKey="Jackson J" first="James E" last="Jackson">James E. Jackson</name><name sortKey="Klinger, Grace E" sort="Klinger, Grace E" uniqKey="Klinger G" first="Grace E" last="Klinger">Grace E. Klinger</name><name sortKey="Klinger, Grace E" sort="Klinger, Grace E" uniqKey="Klinger G" first="Grace E" last="Klinger">Grace E. Klinger</name><name sortKey="Stahl, Shannon S" sort="Stahl, Shannon S" uniqKey="Stahl S" first="Shannon S" last="Stahl">Shannon S. Stahl</name><name sortKey="Stahl, Shannon S" sort="Stahl, Shannon S" uniqKey="Stahl S" first="Shannon S" last="Stahl">Shannon S. Stahl</name><name sortKey="Wester, Abby M" sort="Wester, Abby M" uniqKey="Wester A" first="Abby M" last="Wester">Abby M. Wester</name><name sortKey="Zhou, Yuting" sort="Zhou, Yuting" uniqKey="Zhou Y" first="Yuting" last="Zhou">Yuting Zhou</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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