2. Academic Validation
  3. Systemic Fluorescence Imaging of Zebrafish Glycans with Bioorthogonal Chemistry

Systemic Fluorescence Imaging of Zebrafish Glycans with Bioorthogonal Chemistry

  • Angew Chem Int Ed Engl. 2015 Sep 21;54(39):11504-10. doi: 10.1002/anie.201504249.
Paresh Agarwal 1,  Brendan J Beahm 1,  Peyton Shieh 1,  Carolyn R Bertozzi 2
Affiliations

Affiliations

  • 1 Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, B84 Hildebrand Hall, Berkeley, CA 94720 (USA).
  • 2 Department of Chemistry and Howard Hughes Medical Institute, Stanford University, 333 Campus Drive, Stanford, CA 94305. [email protected].
PMID: 26230529 DOI: 10.1002/anie.201504249
Abstract

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.

Keywords

bioorthogonal chemistry; fluorescent probes; glycans; glycosylation; sialic acids.

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