Publikation:

Rapid glycoconjugation with glycosyl amines

Lade...
Vorschaubild

Dateien

Rapp_2-17krew04xb7b21.pdf
Rapp_2-17krew04xb7b21.pdfGröße: 1.04 MBDownloads: 84

Datum

2021

Herausgeber:innen

Kontakt

ISSN der Zeitschrift

Electronic ISSN

ISBN

Bibliografische Daten

Verlag

Schriftenreihe

Auflagebezeichnung

DOI (zitierfähiger Link)
ArXiv-ID

Internationale Patentnummer

Angaben zur Forschungsförderung

Projekt

Open Access-Veröffentlichung
Open Access Hybrid
Core Facility der Universität Konstanz
NMR Core Facility, Proteomics Centre

Gesperrt bis

Titel in einer weiteren Sprache

Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published

Erschienen in

Chemical Science. Royal Society of Chemistry (RSC). 2021, 12(44), S. 14901-14906. ISSN 2041-6520. eISSN 2041-6539. Verfügbar unter: doi: 10.1039/d1sc05008g

Zusammenfassung

Conjugation of unprotected carbohydrates to surfaces or probes by chemoselective ligation reactions is indispensable for the elucidation of their numerous biological functions. In particular, the reaction with oxyamines leading to the formation of carbohydrate oximes which are in equilibrium with cyclic N-glycosides (oxyamine ligation) has an enormous impact in the field. Although highly chemoselective, the reaction is rather slow. Here, we report that the oxyamine ligation is significantly accelerated without the need for a catalyst when starting with glycosyl amines. Reaction rates are increased up to 500-fold compared to the reaction of the reducing carbohydrate. For comparison, aniline-catalyzed oxyamine ligation is only increased 3.8-fold under the same conditions. Glycosyl amines from mono- and oligosaccharides are easily accessible from reducing carbohydrates via the corresponding azides by using Shoda's reagent (2-chloro-1,3-dimethylimidazolinium chloride, DMC) and subsequent reduction. Furthermore, glycosyl amines are readily obtained by enzymatic release from N-glycoproteins making the method suited for glycomic analysis of these glycoconjugates which we demonstrate employing RNase B. Oxyamine ligation of glycosyl amines can be carried out at close to neutral conditions which makes the procedure especially valuable for acid-sensitive oligosaccharides.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

Konferenz

Rezension
undefined / . - undefined, undefined

Forschungsvorhaben

Organisationseinheiten

Zeitschriftenheft

Zugehörige Datensätze in KOPS

Zitieren

ISO 690RAPP, Mareike A., Oliver R. BAUDENDISTEL, Ulrich STEINER, Valentin WITTMANN, 2021. Rapid glycoconjugation with glycosyl amines. In: Chemical Science. Royal Society of Chemistry (RSC). 2021, 12(44), S. 14901-14906. ISSN 2041-6520. eISSN 2041-6539. Verfügbar unter: doi: 10.1039/d1sc05008g
BibTex
@article{Rapp2021Rapid-55809,
  year={2021},
  doi={10.1039/d1sc05008g},
  title={Rapid glycoconjugation with glycosyl amines},
  number={44},
  volume={12},
  issn={2041-6520},
  journal={Chemical Science},
  pages={14901--14906},
  author={Rapp, Mareike A. and Baudendistel, Oliver R. and Steiner, Ulrich 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/123456789/55809">
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/55809/1/Rapp_2-17krew04xb7b21.pdf"/>
    <dcterms:title>Rapid glycoconjugation with glycosyl amines</dcterms:title>
    <dc:contributor>Rapp, Mareike A.</dc:contributor>
    <dcterms:issued>2021</dcterms:issued>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2021-12-09T09:55:44Z</dcterms:available>
    <dcterms:abstract xml:lang="eng">Conjugation of unprotected carbohydrates to surfaces or probes by chemoselective ligation reactions is indispensable for the elucidation of their numerous biological functions. In particular, the reaction with oxyamines leading to the formation of carbohydrate oximes which are in equilibrium with cyclic N-glycosides (oxyamine ligation) has an enormous impact in the field. Although highly chemoselective, the reaction is rather slow. Here, we report that the oxyamine ligation is significantly accelerated without the need for a catalyst when starting with glycosyl amines. Reaction rates are increased up to 500-fold compared to the reaction of the reducing carbohydrate. For comparison, aniline-catalyzed oxyamine ligation is only increased 3.8-fold under the same conditions. Glycosyl amines from mono- and oligosaccharides are easily accessible from reducing carbohydrates via the corresponding azides by using Shoda's reagent (2-chloro-1,3-dimethylimidazolinium chloride, DMC) and subsequent reduction. Furthermore, glycosyl amines are readily obtained by enzymatic release from N-glycoproteins making the method suited for glycomic analysis of these glycoconjugates which we demonstrate employing RNase B. Oxyamine ligation of glycosyl amines can be carried out at close to neutral conditions which makes the procedure especially valuable for acid-sensitive oligosaccharides.</dcterms:abstract>
    <dc:creator>Wittmann, Valentin</dc:creator>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2021-12-09T09:55:44Z</dc:date>
    <dc:rights>Attribution-NonCommercial 3.0 Unported</dc:rights>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc/3.0/"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/55809/1/Rapp_2-17krew04xb7b21.pdf"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:creator>Steiner, Ulrich</dc:creator>
    <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/55809"/>
    <dc:language>eng</dc:language>
    <dc:contributor>Baudendistel, Oliver R.</dc:contributor>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:contributor>Steiner, Ulrich</dc:contributor>
    <dc:creator>Rapp, Mareike A.</dc:creator>
    <dc:creator>Baudendistel, Oliver R.</dc:creator>
    <dc:contributor>Wittmann, Valentin</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