Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

Schart, Verena F.; Hassenrück, Jessica; Späte, Anne-Katrin; Dold, Jeremias E.G.A.; Fahrner, Raphael; Wittmann, Valentin

Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

Dateien

Schart_2-zr2y892kf8ql1.pdfGröße: 440.89 KBDownloads: 400

Datum

2019

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

ChemBioChem. 2019, 20(2), pp. 166-171. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201800740

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 (DA_inv) 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_inv, photoclick, and copper‐free click chemistry.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

bioorthogonal reactions, carbohydrates, click chemistry, metabolic engineering, tetrazines

Zitieren

ISO 690

SCHART, 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}
}

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