Targeted allylation and propargylation of galactose-containing polysaccharides in water.
Identifieur interne : 000030 ( Main/Exploration ); précédent : 000029; suivant : 000031Targeted allylation and propargylation of galactose-containing polysaccharides in water.
Auteurs : RBID : pubmed:24188837Abstract
Galactose units of spruce galactoglucomannan (GGM), guar galactomannan (GM), and tamarind (galacto)xyloglucan (XG) were selectively allylated. Firstly aldehyde functionalities were formed at the C-6 position via enzymatic oxidation by galactose oxidase. The formed aldehydes were further derivatized by an indium mediated Barbier-Grignard type reaction, resulting in the formation of homoallylic alcohols. In addition to allylic halides, the same reaction procedure was also applicable for GGM, when using propargyl bromide as halide. All reaction steps were done in water, thus the polysaccharides were modified in a one-pot reaction. The formation of the allylated, or propargylated, product was identified by MALDI-TOF-MS. All polysaccharide products were isolated and further characterized by GC-MS or NMR spectroscopy. By this chemo-enzymatic process, we have demonstrated a novel method for derivatization of GGM and other galactose-containing polysaccharides. The derivatized polysaccharides are potential platforms for further functionalizations.
DOI: 10.1016/j.carbpol.2012.11.053
PubMed: 24188837
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Targeted allylation and propargylation of galactose-containing polysaccharides in water.</title><author><name sortKey="Lepp Nen, Ann Sofie" uniqKey="Lepp Nen A">Ann-Sofie Leppänen</name><affiliation wicri:level="1"><nlm:affiliation>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3, FI-20500 Turku, Finland. Electronic address: aleppane@abo.fi.</nlm:affiliation><country xml:lang="fr">Finlande</country><wicri:regionArea>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3, FI-20500 Turku</wicri:regionArea></affiliation></author><author><name sortKey="Xu, Chunlin" uniqKey="Xu C">Chunlin Xu</name></author><author><name sortKey="Parikka, Kirsti" uniqKey="Parikka K">Kirsti Parikka</name></author><author><name sortKey="Eklund, Patrik" uniqKey="Eklund P">Patrik Eklund</name></author><author><name sortKey="Sj Holm, Rainer" uniqKey="Sj Holm R">Rainer Sjöholm</name></author><author><name sortKey="Brumer, Harry" uniqKey="Brumer H">Harry Brumer</name></author><author><name sortKey="Tenkanen, Maija" uniqKey="Tenkanen M">Maija Tenkanen</name></author><author><name sortKey="Willf R, Stefan" uniqKey="Willf R S">Stefan Willför</name></author></titleStmt><publicationStmt><date when="2014">2014</date><idno type="doi">10.1016/j.carbpol.2012.11.053</idno><idno type="RBID">pubmed:24188837</idno><idno type="pmid">24188837</idno><idno type="wicri:Area/Main/Corpus">000331</idno><idno type="wicri:Area/Main/Curation">000331</idno><idno type="wicri:Area/Main/Exploration">000030</idno></publicationStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Galactose units of spruce galactoglucomannan (GGM), guar galactomannan (GM), and tamarind (galacto)xyloglucan (XG) were selectively allylated. Firstly aldehyde functionalities were formed at the C-6 position via enzymatic oxidation by galactose oxidase. The formed aldehydes were further derivatized by an indium mediated Barbier-Grignard type reaction, resulting in the formation of homoallylic alcohols. In addition to allylic halides, the same reaction procedure was also applicable for GGM, when using propargyl bromide as halide. All reaction steps were done in water, thus the polysaccharides were modified in a one-pot reaction. The formation of the allylated, or propargylated, product was identified by MALDI-TOF-MS. All polysaccharide products were isolated and further characterized by GC-MS or NMR spectroscopy. By this chemo-enzymatic process, we have demonstrated a novel method for derivatization of GGM and other galactose-containing polysaccharides. The derivatized polysaccharides are potential platforms for further functionalizations.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="In-Process"><PMID Version="1">24188837</PMID><DateCreated><Year>2013</Year><Month>11</Month><Day>05</Day></DateCreated><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1879-1344</ISSN><JournalIssue CitedMedium="Internet"><Volume>100</Volume><PubDate><Year>2014</Year><Month>Jan</Month><Day>16</Day></PubDate></JournalIssue><Title>Carbohydrate polymers</Title><ISOAbbreviation>Carbohydr Polym</ISOAbbreviation></Journal><ArticleTitle>Targeted allylation and propargylation of galactose-containing polysaccharides in water.</ArticleTitle><Pagination><MedlinePgn>46-54</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.carbpol.2012.11.053</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0144-8617(12)01168-X</ELocationID><Abstract><AbstractText>Galactose units of spruce galactoglucomannan (GGM), guar galactomannan (GM), and tamarind (galacto)xyloglucan (XG) were selectively allylated. Firstly aldehyde functionalities were formed at the C-6 position via enzymatic oxidation by galactose oxidase. The formed aldehydes were further derivatized by an indium mediated Barbier-Grignard type reaction, resulting in the formation of homoallylic alcohols. In addition to allylic halides, the same reaction procedure was also applicable for GGM, when using propargyl bromide as halide. All reaction steps were done in water, thus the polysaccharides were modified in a one-pot reaction. The formation of the allylated, or propargylated, product was identified by MALDI-TOF-MS. All polysaccharide products were isolated and further characterized by GC-MS or NMR spectroscopy. By this chemo-enzymatic process, we have demonstrated a novel method for derivatization of GGM and other galactose-containing polysaccharides. The derivatized polysaccharides are potential platforms for further functionalizations.</AbstractText><CopyrightInformation>Copyright © 2012 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Leppänen</LastName><ForeName>Ann-Sofie</ForeName><Initials>AS</Initials><Affiliation>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3, FI-20500 Turku, Finland. Electronic address: aleppane@abo.fi.</Affiliation></Author><Author ValidYN="Y"><LastName>Xu</LastName><ForeName>Chunlin</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Parikka</LastName><ForeName>Kirsti</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Eklund</LastName><ForeName>Patrik</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Sjöholm</LastName><ForeName>Rainer</ForeName><Initials>R</Initials></Author><Author ValidYN="Y"><LastName>Brumer</LastName><ForeName>Harry</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Tenkanen</LastName><ForeName>Maija</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Willför</LastName><ForeName>Stefan</ForeName><Initials>S</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType><PublicationType>Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2012</Year><Month>11</Month><Day>29</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Carbohydr Polym</MedlineTA><NlmUniqueID>8307156</NlmUniqueID><ISSNLinking>0144-8617</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Allylation</Keyword><Keyword MajorTopicYN="N">Guar galactomannan</Keyword><Keyword MajorTopicYN="N">Indium mediated</Keyword><Keyword MajorTopicYN="N">MALDI-TOF–MS</Keyword><Keyword MajorTopicYN="N">Polysaccharides</Keyword><Keyword MajorTopicYN="N">Propargylation</Keyword><Keyword MajorTopicYN="N">Spruce galactoglucomannan</Keyword><Keyword MajorTopicYN="N">Tamarind xyloglucan</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2012</Year><Month>6</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2012</Year><Month>10</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2012</Year><Month>11</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="aheadofprint"><Year>2012</Year><Month>11</Month><Day>29</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2013</Year><Month>11</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2013</Year><Month>11</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2013</Year><Month>11</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pii">S0144-8617(12)01168-X</ArticleId><ArticleId IdType="doi">10.1016/j.carbpol.2012.11.053</ArticleId><ArticleId IdType="pubmed">24188837</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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