Targeted allylation and propargylation of galactose-containing polysaccharides in water
Identifieur interne : 000025 ( Main/Repository ); précédent : 000024; suivant : 000026Targeted allylation and propargylation of galactose-containing polysaccharides in water
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Abstract
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.
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Targeted allylation and propargylation of galactose-containing polysaccharides in water</title><author><name sortKey="Lepp Nen, Ann Sofie" uniqKey="Lepp Nen A">Ann-Sofie Lepp Nen</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>20500 Turku</wicri:noRegion></affiliation></author><author><name>CHUNLIN XU</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>20500 Turku</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Center</s1><s2>106 91 Stockholm</s2><s3>SWE</s3><sZ>2 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Suède</country><wicri:noRegion>106 91 Stockholm</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Wallenberg Wood Science Center, KTH</s1><s2>100 44 Stockholm</s2><s3>SWE</s3><sZ>2 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Suède</country><wicri:noRegion>100 44 Stockholm</wicri:noRegion></affiliation></author><author><name sortKey="Parikka, Kirsti" uniqKey="Parikka K">Kirsti Parikka</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Food and Environmental Sciences, University of Helsinki, P.O. Box 27</s1><s2>00014 Helsinki</s2><s3>FIN</s3><sZ>3 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>00014 Helsinki</wicri:noRegion></affiliation></author><author><name sortKey="Eklund, Patrik" uniqKey="Eklund P">Patrik Eklund</name><affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>20500 Turku</wicri:noRegion></affiliation></author><author><name sortKey="Sjoholm, Rainer" uniqKey="Sjoholm R">Rainer Sjöholm</name><affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>20500 Turku</wicri:noRegion></affiliation></author><author><name sortKey="Brumer, Harry" uniqKey="Brumer H">Harry Brumer</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Center</s1><s2>106 91 Stockholm</s2><s3>SWE</s3><sZ>2 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Suède</country><wicri:noRegion>106 91 Stockholm</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Wallenberg Wood Science Center, KTH</s1><s2>100 44 Stockholm</s2><s3>SWE</s3><sZ>2 aut.</sZ><sZ>6 aut.</sZ></inist:fA14><country>Suède</country><wicri:noRegion>100 44 Stockholm</wicri:noRegion></affiliation></author><author><name sortKey="Tenkanen, Maija" uniqKey="Tenkanen M">Maija Tenkanen</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Food and Environmental Sciences, University of Helsinki, P.O. Box 27</s1><s2>00014 Helsinki</s2><s3>FIN</s3><sZ>3 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>00014 Helsinki</wicri:noRegion></affiliation></author><author><name sortKey="Willfor, Stefan" uniqKey="Willfor S">Stefan Willför</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Finlande</country><wicri:noRegion>20500 Turku</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="inist">14-0038406</idno><date when="2014">2014</date><idno type="stanalyst">PASCAL 14-0038406 INIST</idno><idno type="RBID">Pascal:14-0038406</idno><idno type="wicri:Area/Main/Corpus">000197</idno><idno type="wicri:Area/Main/Repository">000025</idno></publicationStmt><seriesStmt><idno type="ISSN">0144-8617</idno><title level="j" type="abbreviated">Carbohydr. polym.</title><title level="j" type="main">Carbohydrate polymers</title></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Allylation</term><term>Bromocarbon</term><term>Enzymatic reaction</term><term>Experimental study</term><term>Galactomannan</term><term>Galactose oxidase</term><term>Guar gum</term><term>Indium</term><term>One pot reaction</term><term>Oxidation</term><term>Propargylic compound</term><term>Regioselectivity</term><term>Successive reaction</term><term>Tamarind gum</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Galactomannane</term><term>Gomme tamarin</term><term>Gomme Guar</term><term>Oxydation</term><term>Réaction enzymatique</term><term>Galactose oxidase</term><term>Régiosélectivité</term><term>Réaction successive</term><term>Réaction one pot</term><term>Allylation</term><term>Hydrocarbure bromé</term><term>Composé propargylique</term><term>Indium</term><term>Etude expérimentale</term><term>Galactoglucomannane</term><term>Xyloglucane</term><term>Propargylation</term></keywords></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><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0144-8617</s0></fA01><fA02 i1="01"><s0>CAPOD8</s0></fA02><fA03 i2="1"><s0>Carbohydr. polym.</s0></fA03><fA05><s2>100</s2></fA05><fA06><s2>1</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Targeted allylation and propargylation of galactose-containing polysaccharides in water</s1></fA08><fA11 i1="01" i2="1"><s1>LEPPÄNEN (Ann-Sofie)</s1></fA11><fA11 i1="02" i2="1"><s1>CHUNLIN XU</s1></fA11><fA11 i1="03" i2="1"><s1>PARIKKA (Kirsti)</s1></fA11><fA11 i1="04" i2="1"><s1>EKLUND (Patrik)</s1></fA11><fA11 i1="05" i2="1"><s1>SJÖHOLM (Rainer)</s1></fA11><fA11 i1="06" i2="1"><s1>BRUMER (Harry)</s1></fA11><fA11 i1="07" i2="1"><s1>TENKANEN (Maija)</s1></fA11><fA11 i1="08" i2="1"><s1>WILLFÖR (Stefan)</s1></fA11><fA14 i1="01"><s1>Process Chemistry Centre, Laboratory of Wood and Paper Chemistry, Åbo Akademi University, Porthansgatan 3</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>8 aut.</sZ></fA14><fA14 i1="02"><s1>Division of Glycoscience, School of Biotechnology, Royal Institute of Technology (KTH), AlbaNova University Center</s1><s2>106 91 Stockholm</s2><s3>SWE</s3><sZ>2 aut.</sZ><sZ>6 aut.</sZ></fA14><fA14 i1="03"><s1>Wallenberg Wood Science Center, KTH</s1><s2>100 44 Stockholm</s2><s3>SWE</s3><sZ>2 aut.</sZ><sZ>6 aut.</sZ></fA14><fA14 i1="04"><s1>Department of Food and Environmental Sciences, University of Helsinki, P.O. Box 27</s1><s2>00014 Helsinki</s2><s3>FIN</s3><sZ>3 aut.</sZ><sZ>7 aut.</sZ></fA14><fA14 i1="05"><s1>Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8</s1><s2>20500 Turku</s2><s3>FIN</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></fA14><fA20><s1>46-54</s1></fA20><fA21><s1>2014</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>19272</s2><s5>354000501616200070</s5></fA43><fA44><s0>0000</s0><s1>© 2014 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>3/4 p.</s0></fA45><fA47 i1="01" i2="1"><s0>14-0038406</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Carbohydrate polymers</s0></fA64><fA66 i1="01"><s0>GBR</s0></fA66><fC01 i1="01" l="ENG"><s0>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.</s0></fC01><fC02 i1="01" i2="X"><s0>001D09C04</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Galactomannane</s0><s5>02</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Galactomannan</s0><s5>02</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Galactómanano</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Gomme tamarin</s0><s5>03</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Tamarind gum</s0><s5>03</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Goma tamarín</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="FRE"><s0>Gomme Guar</s0><s5>04</s5></fC03><fC03 i1="03" i2="X" l="ENG"><s0>Guar gum</s0><s5>04</s5></fC03><fC03 i1="03" i2="X" l="SPA"><s0>Goma Guar</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="FRE"><s0>Oxydation</s0><s5>06</s5></fC03><fC03 i1="04" i2="X" l="ENG"><s0>Oxidation</s0><s5>06</s5></fC03><fC03 i1="04" i2="X" l="SPA"><s0>Oxidación</s0><s5>06</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Réaction enzymatique</s0><s5>07</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Enzymatic reaction</s0><s5>07</s5></fC03><fC03 i1="05" i2="X" l="SPA"><s0>Reacción enzimática</s0><s5>07</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Galactose oxidase</s0><s2>FE</s2><s5>08</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Galactose oxidase</s0><s2>FE</s2><s5>08</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Galactose oxidase</s0><s2>FE</s2><s5>08</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Régiosélectivité</s0><s5>09</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Regioselectivity</s0><s5>09</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Regioselectividad</s0><s5>09</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Réaction successive</s0><s5>10</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Successive reaction</s0><s5>10</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Reacción consecutiva</s0><s5>10</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Réaction one pot</s0><s5>11</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>One pot reaction</s0><s5>11</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Reacción one pot</s0><s5>11</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Allylation</s0><s5>12</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Allylation</s0><s5>12</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Alilación</s0><s5>12</s5></fC03><fC03 i1="11" i2="X" l="FRE"><s0>Hydrocarbure bromé</s0><s1>ENT</s1><s5>13</s5></fC03><fC03 i1="11" i2="X" l="ENG"><s0>Bromocarbon</s0><s1>ENT</s1><s5>13</s5></fC03><fC03 i1="11" i2="X" l="SPA"><s0>Hidrocarburo bromado</s0><s1>ENT</s1><s5>13</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Composé propargylique</s0><s1>ENT</s1><s5>14</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Propargylic compound</s0><s1>ENT</s1><s5>14</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Compuesto propargílico</s0><s1>ENT</s1><s5>14</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Indium</s0><s1>ACT</s1><s2>NC</s2><s5>15</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Indium</s0><s1>ACT</s1><s2>NC</s2><s5>15</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Indio</s0><s1>ACT</s1><s2>NC</s2><s5>15</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>Etude expérimentale</s0><s5>18</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>Experimental study</s0><s5>18</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>Estudio experimental</s0><s5>18</s5></fC03><fC03 i1="15" i2="X" l="FRE"><s0>Galactoglucomannane</s0><s2>NK</s2><s4>INC</s4><s5>32</s5></fC03><fC03 i1="16" i2="X" l="FRE"><s0>Xyloglucane</s0><s2>NK</s2><s4>INC</s4><s5>33</s5></fC03><fC03 i1="17" i2="X" l="FRE"><s0>Propargylation</s0><s4>INC</s4><s5>34</s5></fC03><fC07 i1="01" i2="X" l="FRE"><s0>Oside polymère</s0><s2>NK</s2><s5>01</s5></fC07><fC07 i1="01" i2="X" l="ENG"><s0>Oside polymer</s0><s2>NK</s2><s5>01</s5></fC07><fC07 i1="01" i2="X" l="SPA"><s0>Osido polímero</s0><s2>NK</s2><s5>01</s5></fC07><fC07 i1="02" i2="X" l="FRE"><s0>Oxidoreductases</s0><s2>FE</s2></fC07><fC07 i1="02" i2="X" l="ENG"><s0>Oxidoreductases</s0><s2>FE</s2></fC07><fC07 i1="02" i2="X" l="SPA"><s0>Oxidoreductases</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="FRE"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="ENG"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="SPA"><s0>Enzima</s0><s2>FE</s2></fC07><fN21><s1>041</s1></fN21><fN44 i1="01"><s1>PSI</s1></fN44><fN82><s1>PSI</s1></fN82></pA></standard></inist></record>Pour manipuler ce document sous Unix (Dilib)
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