Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

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

@article{Schart2019-01-18Tripl-44584, title={Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry}, year={2019}, doi={10.1002/cbic.201800740}, 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} }

Dold, Jeremias E. G. A. Wittmann, Valentin Späte, Anne-Katrin Fahrner, Raphael Schart, Verena F. terms-of-use 2019-01-18 Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry eng 2019-01-16T09:00:10Z Hassenrück, Jessica Dold, Jeremias E. G. A. Fahrner, Raphael 2019-01-16T09:00:10Z Späte, Anne-Katrin Schart, Verena F. 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<sub>inv</sub>) 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<sub>inv</sub>, photoclick, and copper‐free click chemistry. Hassenrück, Jessica Wittmann, Valentin

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