Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.
Identifieur interne : 000F81 ( PubMed/Corpus ); précédent : 000F80; suivant : 000F82Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.
Auteurs : Heung Sik Hahm ; Mattan Hurevich ; Peter H. SeebergerSource :
- Nature communications [ 2041-1723 ] ; 2016.
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 trans-glycosidic linkages, where C2 participating protecting groups ensure stereoselective couplings. Stereocontrol during the installation of cis-glycosidic linkages cannot rely on C2-participation and anomeric mixtures are typically formed. Here, we demonstrate that oligosaccharides containing multiple cis-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 cis-galactosidic and cis-glucosidic linkages. This work provides further proof that AGA facilitates the synthesis of complex oligosaccharides with multiple cis-linkages and other biologically important oligosaccharides.
DOI: 10.1038/ncomms12482
PubMed: 27580973
Links to Exploration step
pubmed:27580973Le document en format XML
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Seeberger</name><affiliation><nlm:affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</nlm:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:27580973</idno><idno type="pmid">27580973</idno><idno type="doi">10.1038/ncomms12482</idno><idno type="wicri:Area/PubMed/Corpus">000F81</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000F81</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.</title><author><name sortKey="Hahm, Heung Sik" sort="Hahm, Heung Sik" uniqKey="Hahm H" first="Heung Sik" last="Hahm">Heung Sik Hahm</name><affiliation><nlm:affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</nlm:affiliation></affiliation></author><author><name sortKey="Hurevich, Mattan" sort="Hurevich, Mattan" uniqKey="Hurevich M" first="Mattan" last="Hurevich">Mattan Hurevich</name><affiliation><nlm:affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</nlm:affiliation></affiliation></author><author><name sortKey="Seeberger, Peter H" sort="Seeberger, Peter H" uniqKey="Seeberger P" first="Peter H" last="Seeberger">Peter H. Seeberger</name><affiliation><nlm:affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Nature communications</title><idno type="eISSN">2041-1723</idno><imprint><date when="2016" type="published">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="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" xml:lang="en"><term>Glycosylation</term><term>Stereoisomerism</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">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 trans-glycosidic linkages, where C2 participating protecting groups ensure stereoselective couplings. Stereocontrol during the installation of cis-glycosidic linkages cannot rely on C2-participation and anomeric mixtures are typically formed. Here, we demonstrate that oligosaccharides containing multiple cis-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 cis-galactosidic and cis-glucosidic linkages. This work provides further proof that AGA facilitates the synthesis of complex oligosaccharides with multiple cis-linkages and other biologically important oligosaccharides.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27580973</PMID><DateCompleted><Year>2018</Year><Month>09</Month><Day>03</Day></DateCompleted><DateRevised><Year>2019</Year><Month>04</Month><Day>23</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">2041-1723</ISSN><JournalIssue CitedMedium="Internet"><Volume>7</Volume><PubDate><Year>2016</Year><Month>09</Month><Day>01</Day></PubDate></JournalIssue><Title>Nature communications</Title><ISOAbbreviation>Nat Commun</ISOAbbreviation></Journal><ArticleTitle>Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.</ArticleTitle><Pagination><MedlinePgn>12482</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1038/ncomms12482</ELocationID><Abstract><AbstractText>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 trans-glycosidic linkages, where C2 participating protecting groups ensure stereoselective couplings. Stereocontrol during the installation of cis-glycosidic linkages cannot rely on C2-participation and anomeric mixtures are typically formed. Here, we demonstrate that oligosaccharides containing multiple cis-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 cis-galactosidic and cis-glucosidic linkages. This work provides further proof that AGA facilitates the synthesis of complex oligosaccharides with multiple cis-linkages and other biologically important oligosaccharides.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Hahm</LastName><ForeName>Heung Sik</ForeName><Initials>HS</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-2326-7923</Identifier><AffiliationInfo><Affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, Berlin 14195, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hurevich</LastName><ForeName>Mattan</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Seeberger</LastName><ForeName>Peter H</ForeName><Initials>PH</Initials><AffiliationInfo><Affiliation>Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, Berlin 14195, Germany.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><Agency>European Research Council</Agency><Country>International</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>09</Month><Day>01</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Nat Commun</MedlineTA><NlmUniqueID>101528555</NlmUniqueID><ISSNLinking>2041-1723</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005697">Galactosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005960">Glucosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009005">Monosaccharides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009844">Oligosaccharides</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D057205" MajorTopicYN="N">Automation, Laboratory</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="N">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005697" MajorTopicYN="N">Galactosides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005960" MajorTopicYN="N">Glucosides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006031" MajorTopicYN="N">Glycosylation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009005" MajorTopicYN="N">Monosaccharides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009844" MajorTopicYN="N">Oligosaccharides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList><CoiStatement>P.H.S. is a shareholder of GlycoUniverse, a company involved in automated carbohydrate synthesis. H.S.H. and M.H. declare no competing financial interest.</CoiStatement></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>04</Month><Day>28</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2016</Year><Month>07</Month><Day>06</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>9</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>9</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2018</Year><Month>9</Month><Day>4</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27580973</ArticleId><ArticleId IdType="pii">ncomms12482</ArticleId><ArticleId IdType="doi">10.1038/ncomms12482</ArticleId><ArticleId 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