Synthesis of Sulfonamide-Bridged Glycomimetics
Identifieur interne : 006683 ( Main/Exploration ); précédent : 006682; suivant : 006684Synthesis of Sulfonamide-Bridged Glycomimetics
Auteurs : Marie Lopez [Australie] ; Laurent F. Bornaghi [Australie] ; Hugues Driguez [France] ; Sally-Ann Poulsen [Australie]Source :
- Journal of organic chemistry [ 0022-3263 ] ; 2011.
Descripteurs français
- Pascal (Inist)
English descriptors
- KwdEn :
Abstract
A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1↔1) and head-to-tail (1→2), (1→3), (1→4), and (1→6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream PascalFrancis, to step Corpus: 001A81
- to stream PascalFrancis, to step Curation: 004463
- to stream PascalFrancis, to step Checkpoint: 001633
- to stream Main, to step Merge: 006A84
- to stream Main, to step Curation: 006683
Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Synthesis of Sulfonamide-Bridged Glycomimetics</title>
<author><name sortKey="Lopez, Marie" sort="Lopez, Marie" uniqKey="Lopez M" first="Marie" last="Lopez">Marie Lopez</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1>
<s2>Queensland, 4111</s2>
<s3>AUS</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Australie</country>
<wicri:noRegion>Queensland, 4111</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Bornaghi, Laurent F" sort="Bornaghi, Laurent F" uniqKey="Bornaghi L" first="Laurent F." last="Bornaghi">Laurent F. Bornaghi</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1>
<s2>Queensland, 4111</s2>
<s3>AUS</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Australie</country>
<wicri:noRegion>Queensland, 4111</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Driguez, Hugues" sort="Driguez, Hugues" uniqKey="Driguez H" first="Hugues" last="Driguez">Hugues Driguez</name>
<affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Centre de Recherche sur les Macromolécules Végétales, UPR-CNRS 5301, BP53</s1>
<s2>38041 Grenoble</s2>
<s3>FRA</s3>
<sZ>3 aut.</sZ>
</inist:fA14>
<country>France</country>
<wicri:noRegion>38041 Grenoble</wicri:noRegion>
<placeName><settlement type="city">Grenoble</settlement>
<region type="region" nuts="2">Auvergne-Rhône-Alpes</region>
<region type="old region" nuts="2">Rhône-Alpes</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Poulsen, Sally Ann" sort="Poulsen, Sally Ann" uniqKey="Poulsen S" first="Sally-Ann" last="Poulsen">Sally-Ann Poulsen</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1>
<s2>Queensland, 4111</s2>
<s3>AUS</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Australie</country>
<wicri:noRegion>Queensland, 4111</wicri:noRegion>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">INIST</idno>
<idno type="inist">11-0339950</idno>
<date when="2011">2011</date>
<idno type="stanalyst">PASCAL 11-0339950 INIST</idno>
<idno type="RBID">Pascal:11-0339950</idno>
<idno type="wicri:Area/PascalFrancis/Corpus">001A81</idno>
<idno type="wicri:Area/PascalFrancis/Curation">004463</idno>
<idno type="wicri:Area/PascalFrancis/Checkpoint">001633</idno>
<idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">001633</idno>
<idno type="wicri:doubleKey">0022-3263:2011:Lopez M:synthesis:of:sulfonamide</idno>
<idno type="wicri:Area/Main/Merge">006A84</idno>
<idno type="wicri:Area/Main/Curation">006683</idno>
<idno type="wicri:Area/Main/Exploration">006683</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Synthesis of Sulfonamide-Bridged Glycomimetics</title>
<author><name sortKey="Lopez, Marie" sort="Lopez, Marie" uniqKey="Lopez M" first="Marie" last="Lopez">Marie Lopez</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1>
<s2>Queensland, 4111</s2>
<s3>AUS</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Australie</country>
<wicri:noRegion>Queensland, 4111</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Bornaghi, Laurent F" sort="Bornaghi, Laurent F" uniqKey="Bornaghi L" first="Laurent F." last="Bornaghi">Laurent F. Bornaghi</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1>
<s2>Queensland, 4111</s2>
<s3>AUS</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Australie</country>
<wicri:noRegion>Queensland, 4111</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Driguez, Hugues" sort="Driguez, Hugues" uniqKey="Driguez H" first="Hugues" last="Driguez">Hugues Driguez</name>
<affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Centre de Recherche sur les Macromolécules Végétales, UPR-CNRS 5301, BP53</s1>
<s2>38041 Grenoble</s2>
<s3>FRA</s3>
<sZ>3 aut.</sZ>
</inist:fA14>
<country>France</country>
<wicri:noRegion>38041 Grenoble</wicri:noRegion>
<placeName><settlement type="city">Grenoble</settlement>
<region type="region" nuts="2">Auvergne-Rhône-Alpes</region>
<region type="old region" nuts="2">Rhône-Alpes</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Poulsen, Sally Ann" sort="Poulsen, Sally Ann" uniqKey="Poulsen S" first="Sally-Ann" last="Poulsen">Sally-Ann Poulsen</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eskitis Institute, Griffith University, Nathan Campus</s1>
<s2>Queensland, 4111</s2>
<s3>AUS</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
</inist:fA14>
<country>Australie</country>
<wicri:noRegion>Queensland, 4111</wicri:noRegion>
</affiliation>
</author>
</analytic>
<series><title level="j" type="main">Journal of organic chemistry</title>
<title level="j" type="abbreviated">J. org. chem.</title>
<idno type="ISSN">0022-3263</idno>
<imprint><date when="2011">2011</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
<seriesStmt><title level="j" type="main">Journal of organic chemistry</title>
<title level="j" type="abbreviated">J. org. chem.</title>
<idno type="ISSN">0022-3263</idno>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminosugar</term>
<term>Anomer</term>
<term>Chemical synthesis</term>
<term>Configuration retention</term>
<term>Glycomimetic compound</term>
<term>Glycoside</term>
<term>Oside</term>
<term>Protecting group</term>
<term>Stereochemistry</term>
<term>Sulfonamide</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term>
<term>Sulfonamide</term>
<term>Glycoside</term>
<term>Ose amine</term>
<term>Rétention configuration</term>
<term>Anomère</term>
<term>Stéréochimie</term>
<term>Groupe protecteur</term>
<term>Oside</term>
<term>Thioacétique acide dérivé</term>
<term>Composé glycomimétique</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1↔1) and head-to-tail (1→2), (1→3), (1→4), and (1→6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.</div>
</front>
</TEI>
<affiliations><list><country><li>Australie</li>
<li>France</li>
</country>
<region><li>Auvergne-Rhône-Alpes</li>
<li>Rhône-Alpes</li>
</region>
<settlement><li>Grenoble</li>
</settlement>
</list>
<tree><country name="Australie"><noRegion><name sortKey="Lopez, Marie" sort="Lopez, Marie" uniqKey="Lopez M" first="Marie" last="Lopez">Marie Lopez</name>
</noRegion>
<name sortKey="Bornaghi, Laurent F" sort="Bornaghi, Laurent F" uniqKey="Bornaghi L" first="Laurent F." last="Bornaghi">Laurent F. Bornaghi</name>
<name sortKey="Poulsen, Sally Ann" sort="Poulsen, Sally Ann" uniqKey="Poulsen S" first="Sally-Ann" last="Poulsen">Sally-Ann Poulsen</name>
</country>
<country name="France"><region name="Auvergne-Rhône-Alpes"><name sortKey="Driguez, Hugues" sort="Driguez, Hugues" uniqKey="Driguez H" first="Hugues" last="Driguez">Hugues Driguez</name>
</region>
</country>
</tree>
</affiliations>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Asie/explor/AustralieFrV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 006683 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 006683 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Wicri/Asie |area= AustralieFrV1 |flux= Main |étape= Exploration |type= RBID |clé= Pascal:11-0339950 |texte= Synthesis of Sulfonamide-Bridged Glycomimetics }}
![]() | This area was generated with Dilib version V0.6.33. | ![]() |