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Bioconjug Chem. 2014 Jan 15;25(1):147-54. doi: 10.1021/bc4004487. Epub 2013 Dec 24.

Rapid labeling of metabolically engineered cell-surface glycoconjugates with a carbamate-linked cyclopropene reporter.

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  • 1University of Konstanz , Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), Universitätsstraße 10, 78457 Konstanz, Germany.


Metabolic oligosaccharide engineering is a valuable tool to monitor cellular carbohydrates. Here, we report the synthesis of a novel N-acyl-mannosamine derivative bearing a methylcyclopropene tag that is attached to the sugar via a carbamate moiety. This derivative undergoes rapid Diels-Alder reaction with inverse electron demand. We demonstrate that the cell's biosynthetic machinery incorporates this non-natural mannosamine derivative into glycoconjugates that can, subsequently, be labeled within less than 10 min with a new sulfo-Cy3-tetrazine conjugate. Using this tetrazine-dye conjugate for the detection of the methylcyclopropene-tagged mannosamine derivative, we could achieve dual labeling of two different metabolically incorporated sugars combining a Diels-Alder reaction with inverse electron demand and a strain-promoted azide-alkyne cycloaddition which are carried out simultaneously in a single step.

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