title: Systemic Fluorescence Imaging of Zebrafish Glycans with Bioorthogonal Chemistry.
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.
authors.affiliation: Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, B84 Hildebrand Hall, Berkeley, CA 94720 (USA).
authors.forename: Paresh
authors.initials: P
authors.lastname: Agarwal
authors.affiliation: Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, B84 Hildebrand Hall, Berkeley, CA 94720 (USA).
authors.forename: Brendan J
authors.initials: BJ
authors.lastname: Beahm
authors.affiliation: Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, Berkeley, B84 Hildebrand Hall, Berkeley, CA 94720 (USA).
authors.forename: Peyton
authors.initials: P
authors.lastname: Shieh
authors.affiliation: Department of Chemistry and Howard Hughes Medical Institute, Stanford University, 333 Campus Drive, Stanford, CA 94305. bertozzi@stanford.edu.
authors.forename: Carolyn R
authors.initials: CR
authors.lastname: Bertozzi
mesh_terms: D000818:Animals; D006031:Glycosylation; D057809:HEK293 Cells; D006801:Humans; D008856:Microscopy, Fluorescence / Q000379:methods*; D011134:Polysaccharides / Q000737:chemistry / Q000378:metabolism*; D015027:Zebrafish / Q000196:embryology
chemical_list: D011134:Polysaccharides
keywords: bioorthogonal chemistry; fluorescent probes; glycans; glycosylation; sialic acids