Rapid Labeling of Metabolically Engineered Cell-Surface Glycoconjugates with a Carbamate-Linked Cyclopropene Reporter

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Bioconjugate Chemistry. 2014, 25(1), pp. 147-154. ISSN 1043-1802. eISSN 1520-4812. Available under: doi: 10.1021/bc4004487
Zusammenfassung

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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ISO 690SPÄTE, Anne-Katrin, Holger BUSSKAMP, Andrea NIEDERWIESER, Verena F. SCHART, Andreas MARX, Valentin WITTMANN, 2014. Rapid Labeling of Metabolically Engineered Cell-Surface Glycoconjugates with a Carbamate-Linked Cyclopropene Reporter. In: Bioconjugate Chemistry. 2014, 25(1), pp. 147-154. ISSN 1043-1802. eISSN 1520-4812. Available under: doi: 10.1021/bc4004487
BibTex
@article{Spate2014-01-15Rapid-25945,
  year={2014},
  doi={10.1021/bc4004487},
  title={Rapid Labeling of Metabolically Engineered Cell-Surface Glycoconjugates with a Carbamate-Linked Cyclopropene Reporter},
  number={1},
  volume={25},
  issn={1043-1802},
  journal={Bioconjugate Chemistry},
  pages={147--154},
  author={Späte, Anne-Katrin and Bußkamp, Holger and Niederwieser, Andrea and Schart, Verena F. and Marx, Andreas and Wittmann, Valentin}
}
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