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Systemic Fluorescence Imaging of Zebrafish Glycans with Bioorthogonal Chemistry
Author(s) -
Agarwal Paresh,
Beahm Brendan J.,
Shieh Peyton,
Bertozzi Carolyn R.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504249
Subject(s) - bioorthogonal chemistry , glycan , chemistry , glycoconjugate , zebrafish , glycosylation , sialic acid , fluorescence , live cell imaging , click chemistry , biochemistry , combinatorial chemistry , glycoprotein , physics , quantum mechanics , cell , gene
Vertebrate glycans constitute a large, important, and dynamic set of post‐translational modifications that are notoriously difficult to manipulate and image. Although the chemical reporter strategy has been used in conjunction with bioorthogonal chemistry to image the external glycosylation state of live zebrafish and detect tumor‐associated glycans in mice, the ability to image glycans systemically within a live organism has remained elusive. Here, we report a method that combines the metabolic incorporation of a cyclooctyne‐functionalized sialic acid derivative with a ligation reaction of a fluorogenic tetrazine, allowing for the imaging of sialylated glycoconjugates within live zebrafish embryos.