Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels-Alder reactions

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Beilstein Journal of Organic Chemistry. 2014, 10, pp. 2235-2242. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.3762/bjoc.10.232
Zusammenfassung

Monitoring glycoconjugates has been tremendously facilitated by the development of metabolic oligosaccharide engineering. Recently, the inverse-electron-demand Diels–Alder reaction between methylcyclopropene tags and tetrazines has become a popular ligation reaction due to the small size and high reactivity of cyclopropene tags. Attaching the cyclopropene tag to mannosamine via a carbamate linkage has made the reaction even more efficient. Here, we expand the application of cyclopropene tags to N-acylgalactosamine and N-acylglucosamine derivatives enabling the visualization of mucin-type O-glycoproteins and O-GlcNAcylated proteins through Diels–Alder chemistry. Whereas the previously reported cyclopropene-labeled N-acylmannosamine derivative leads to significantly higher fluorescence staining of cell-surface glycoconjugates, the glucosamine derivative gave higher labeling efficiency with protein preparations containing also intracellular proteins.

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540 Chemie
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bioorthogonal chemistry, carbohydrates, cyclopropenes, inverse-electron-demand Diels-Alder reactions, metabolic oligosaccharide engineering
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ISO 690SPÄTE, Anne-Katrin, Verena F. SCHART, Julia HÄFNER, Andrea NIEDERWIESER, Thomas U. MAYER, Valentin WITTMANN, 2014. Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels-Alder reactions. In: Beilstein Journal of Organic Chemistry. 2014, 10, pp. 2235-2242. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.3762/bjoc.10.232
BibTex
@article{Spate2014Expan-29320,
  year={2014},
  doi={10.3762/bjoc.10.232},
  title={Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels-Alder reactions},
  volume={10},
  issn={0022-3263},
  journal={Beilstein Journal of Organic Chemistry},
  pages={2235--2242},
  author={Späte, Anne-Katrin and Schart, Verena F. and Häfner, Julia and Niederwieser, Andrea and Mayer, Thomas U. and Wittmann, Valentin}
}
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