Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages
Identifieur interne : 001366 ( Main/Exploration ); précédent : 001365; suivant : 001367Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages
Auteurs : Heung Sik Hahm [Allemagne] ; Mattan Hurevich [Allemagne] ; Peter H. Seeberger [Allemagne]Source :
- Nature Communications [ 2041-1723 ] ; 2016.
Descripteurs français
- KwdFr :
- MESH :
- synthèse chimique : Oligosaccharides.
- Galactoside, Glucosides, Glycosylation, Laboratoire automatique, Oses, Stéréoisomérie.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Oligosaccharides.
- chemical , chemistry : Galactosides, Glucosides, Monosaccharides.
- methods : Automation, Laboratory.
- Glycosylation, Stereoisomerism.
Abstract
Automated glycan assembly (AGA) has advanced from a concept to a commercial technology that rapidly provides access to diverse oligosaccharide chains as long as 30-mers. To date, AGA was mainly employed to incorporate
Url:
DOI: 10.1038/ncomms12482
PubMed: 27580973
PubMed Central: 5025749
Affiliations:
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Le document en format XML
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Seeberger</name><affiliation wicri:level="1"><nlm:aff id="a1"><institution>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces</institution>, Am Mühlenberg 1, Potsdam 14424,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="a2"><institution>Institute of Chemistry and Biochemistry, Freie Universität Berlin</institution>, Arnimallee 22, Berlin 14195,<country>Germany</country></nlm:aff><country xml:lang="fr">Allemagne</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">Nature Communications</title><idno type="eISSN">2041-1723</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Automation, Laboratory (methods)</term><term>Galactosides (chemistry)</term><term>Glucosides (chemistry)</term><term>Glycosylation</term><term>Monosaccharides (chemistry)</term><term>Oligosaccharides (chemical synthesis)</term><term>Stereoisomerism</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Galactoside ()</term><term>Glucosides ()</term><term>Glycosylation</term><term>Laboratoire automatique ()</term><term>Oligosaccharides (synthèse chimique)</term><term>Oses ()</term><term>Stéréoisomérie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligosaccharides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Galactosides</term><term>Glucosides</term><term>Monosaccharides</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Automation, Laboratory</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Oligosaccharides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Glycosylation</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Galactoside</term><term>Glucosides</term><term>Glycosylation</term><term>Laboratoire automatique</term><term>Oses</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Automated glycan assembly (AGA) has advanced from a concept to a commercial technology that rapidly provides access to diverse oligosaccharide chains as long as 30-mers. To date, AGA was mainly employed to incorporate <italic>trans</italic>-glycosidic linkages, where C2 participating protecting groups ensure stereoselective couplings. Stereocontrol during the installation of <italic>cis</italic>-glycosidic linkages cannot rely on C2-participation and anomeric mixtures are typically formed. Here, we demonstrate that oligosaccharides containing multiple <italic>cis-</italic>glycosidic linkages can be prepared efficiently by AGA using monosaccharide building blocks equipped with remote participating protecting groups. The concept is illustrated by the automated syntheses of biologically relevant oligosaccharides bearing various <italic>cis</italic>-galactosidic and <italic>cis</italic>-glucosidic linkages. This work provides further proof that AGA facilitates the synthesis of complex oligosaccharides with multiple <italic>cis-</italic>linkages and other biologically important oligosaccharides.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Dwek, R A" uniqKey="Dwek R">R. A. Dwek</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Plante, O J" uniqKey="Plante O">O. J. Plante</name></author><author><name sortKey="Palmacci, E R" uniqKey="Palmacci E">E. R. Palmacci</name></author><author><name sortKey="Seeberger, P H" uniqKey="Seeberger P">P. H. Seeberger</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Seeberger, P H" uniqKey="Seeberger P">P. H. Seeberger</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Krock, L" uniqKey="Krock L">L. 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Wang</name></author><author><name sortKey="Zhou, L" uniqKey="Zhou L">L. Zhou</name></author><author><name sortKey="El Boubbou, K" uniqKey="El Boubbou K">K. El-Boubbou</name></author><author><name sortKey="Ye, X S" uniqKey="Ye X">X.-S. Ye</name></author><author><name sortKey="Huang, X" uniqKey="Huang X">X. Huang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Gilewski, T" uniqKey="Gilewski T">T. Gilewski</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wilson, R M" uniqKey="Wilson R">R. M. Wilson</name></author><author><name sortKey="Danishefsky, S J" uniqKey="Danishefsky S">S. J. Danishefsky</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Zhao, C" uniqKey="Zhao C">C. Zhao</name></author><author><name sortKey="Li, M" uniqKey="Li M">M. Li</name></author><author><name sortKey="Luo, Y" uniqKey="Luo Y">Y. Luo</name></author><author><name sortKey="Wu, W" uniqKey="Wu W">W. Wu</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Bittencourt, V C B" uniqKey="Bittencourt V">V. C. B. Bittencourt</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Allemagne</li></country></list><tree><country name="Allemagne"><noRegion><name sortKey="Hahm, Heung Sik" sort="Hahm, Heung Sik" uniqKey="Hahm H" first="Heung Sik" last="Hahm">Heung Sik Hahm</name></noRegion><name sortKey="Hahm, Heung Sik" sort="Hahm, Heung Sik" uniqKey="Hahm H" first="Heung Sik" last="Hahm">Heung Sik Hahm</name><name sortKey="Hurevich, Mattan" sort="Hurevich, Mattan" uniqKey="Hurevich M" first="Mattan" last="Hurevich">Mattan Hurevich</name><name sortKey="Seeberger, Peter H" sort="Seeberger, Peter H" uniqKey="Seeberger P" first="Peter H" last="Seeberger">Peter H. Seeberger</name><name sortKey="Seeberger, Peter H" sort="Seeberger, Peter H" uniqKey="Seeberger P" first="Peter H" last="Seeberger">Peter H. 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