Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

Lade...
Vorschaubild
Dateien
Schart_2-zr2y892kf8ql1.pdf
Schart_2-zr2y892kf8ql1.pdfGröße: 440.89 KBDownloads: 403
Datum
2019
Herausgeber:innen
Kontakt
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
ArXiv-ID
Internationale Patentnummer
Angaben zur Forschungsförderung
Projekt
Open Access-Veröffentlichung
Open Access Green
Sammlungen
Core Facility der Universität Konstanz
Gesperrt bis
Titel in einer weiteren Sprache
Forschungsvorhaben
Organisationseinheiten
Zeitschriftenheft
Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published
Erschienen in
Zusammenfassung

Bioorthogonal labeling of multiple biomolecules is of current interest in chemical biology. Metabolic glycoengineering (MGE) has been shown to be an appropriate approach to visualizing carbohydrates. Here, we report that the nitrile imine–alkene cycloaddition (photoclick reaction) is a suitable ligation reaction in MGE. Using a mannosamine derivative with an acrylamide reporter group that is efficiently metabolized by cells and that quickly reacts in the photoclick reaction, we labeled sialic acids on the surface of living cells. Screening of several alkenes showed that a previously reported carbamate‐linked methylcyclopropene reporter that is well suited for the inverse‐electron‐demand Diels–Alder (DAinv) reaction has a surprisingly low reactivity in the photoclick reaction. Thus, for the first time, we were able to triply label glycans by a combination of DAinv, photoclick, and copper‐free click chemistry.

Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
Schlagwörter
bioorthogonal reactions, carbohydrates, click chemistry, metabolic engineering, tetrazines
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690SCHART, Verena F., Jessica HASSENRÜCK, Anne-Katrin SPÄTE, Jeremias E.G.A. DOLD, Raphael FAHRNER, Valentin WITTMANN, 2019. Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry. In: ChemBioChem. 2019, 20(2), pp. 166-171. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201800740
BibTex
@article{Schart2019-01-18Tripl-44584,
  year={2019},
  doi={10.1002/cbic.201800740},
  title={Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry},
  number={2},
  volume={20},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={166--171},
  author={Schart, Verena F. and Hassenrück, Jessica and Späte, Anne-Katrin and Dold, Jeremias E.G.A. and Fahrner, Raphael and Wittmann, Valentin}
}
RDF
<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/44584">
    <dc:creator>Wittmann, Valentin</dc:creator>
    <dcterms:title>Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry</dcterms:title>
    <dc:contributor>Späte, Anne-Katrin</dc:contributor>
    <dc:creator>Hassenrück, Jessica</dc:creator>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:contributor>Fahrner, Raphael</dc:contributor>
    <dc:creator>Späte, Anne-Katrin</dc:creator>
    <dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/44584/1/Schart_2-zr2y892kf8ql1.pdf"/>
    <dcterms:abstract xml:lang="eng">Bioorthogonal labeling of multiple biomolecules is of current interest in chemical biology. Metabolic glycoengineering (MGE) has been shown to be an appropriate approach to visualizing carbohydrates. Here, we report that the nitrile imine–alkene cycloaddition (photoclick reaction) is a suitable ligation reaction in MGE. Using a mannosamine derivative with an acrylamide reporter group that is efficiently metabolized by cells and that quickly reacts in the photoclick reaction, we labeled sialic acids on the surface of living cells. Screening of several alkenes showed that a previously reported carbamate‐linked methylcyclopropene reporter that is well suited for the inverse‐electron‐demand Diels–Alder (DA&lt;sub&gt;inv&lt;/sub&gt;) reaction has a surprisingly low reactivity in the photoclick reaction. Thus, for the first time, we were able to triply label glycans by a combination of DA&lt;sub&gt;inv&lt;/sub&gt;, photoclick, and copper‐free click chemistry.</dcterms:abstract>
    <dc:contributor>Wittmann, Valentin</dc:contributor>
    <dc:contributor>Dold, Jeremias E.G.A.</dc:contributor>
    <dc:creator>Fahrner, Raphael</dc:creator>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/44584/1/Schart_2-zr2y892kf8ql1.pdf"/>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Dold, Jeremias E.G.A.</dc:creator>
    <dc:rights>terms-of-use</dc:rights>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-01-16T09:00:10Z</dcterms:available>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:contributor>Schart, Verena F.</dc:contributor>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-01-16T09:00:10Z</dc:date>
    <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/44584"/>
    <dc:language>eng</dc:language>
    <dc:creator>Schart, Verena F.</dc:creator>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:issued>2019-01-18</dcterms:issued>
    <dc:contributor>Hassenrück, Jessica</dc:contributor>
  </rdf:Description>
</rdf:RDF>
Interner Vermerk
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Kontakt
URL der Originalveröffentl.
Prüfdatum der URL
Prüfungsdatum der Dissertation
Finanzierungsart
Kommentar zur Publikation
Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Ja
Begutachtet
Ja
Diese Publikation teilen