Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

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 liga...

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Published in:Chembiochem : a European journal of chemical biology 2019-01, Vol.20 (2), p.166-171
Main Authors: Schart, Verena F., Hassenrück, Jessica, Späte, Anne‐Katrin, Dold, Jeremias E. G. A., Fahrner, Raphael, Wittmann, Valentin
Format: Article
Language:English
Subjects:
Acrylamide
Alkenes
Biomolecules
bioorthogonal reactions
Carbohydrates
Chemical synthesis
click chemistry
Cycloaddition
Labeling
metabolic engineering
Organic chemistry
Polysaccharides
Sialic acids
tetrazines
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Summary: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. All good things come in threes: The nitrile imine–alkene cycloaddition (photoclick reaction) was shown to be a suitable ligation reaction for metabolic glycoengineering. In combination with an inverse‐electron‐demand Diels–Alder reaction and strain‐promoted azide–alkyne cycloaddition, triple labeling of glycans was achieved for the first time.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.201800740