@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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    <dc:contributor>Niederwieser, Andrea</dc:contributor>
    <dc:creator>Mayer, Thomas U.</dc:creator>
    <dc:contributor>Späte, Anne-Katrin</dc:contributor>
    <dcterms:title>Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels-Alder reactions</dcterms:title>
    <dc:creator>Schart, Verena F.</dc:creator>
    <dc:contributor>Wittmann, Valentin</dc:contributor>
    <dc:contributor>Häfner, Julia</dc:contributor>
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    <dcterms:issued>2014</dcterms:issued>
    <dc:creator>Häfner, Julia</dc:creator>
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    <dc:contributor>Schart, Verena F.</dc:contributor>
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    <dc:language>eng</dc:language>
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    <dcterms:abstract xml:lang="eng">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.</dcterms:abstract>
    <dc:contributor>Mayer, Thomas U.</dc:contributor>
    <dc:creator>Niederwieser, Andrea</dc:creator>
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    <dc:creator>Späte, Anne-Katrin</dc:creator>
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