title: Light-Activated Staudinger-Bertozzi Ligation within Living Animals.
abstract: The ability to regulate small molecule chemistry in vivo will enable new avenues of exploration in imaging and pharmacology. However, realization of these goals will require reactions with high specificity and precise control. Here we demonstrate photocontrol over the highly specific Staudinger-Bertozzi ligation in vitro and in vivo. Our simple approach, photocaging the key phosphine atom, allows for the facile production of reagents with photochemistry that can be engineered for specific applications. The resulting compounds, which are both stable and efficiently activated, enable the spatial labeling of metabolically introduced azides in vitro and on live zebrafish.
authors.affiliation: Department of Chemistry and ‡Institute of Chemical Biology and Drug Discovery, State University of New York Stony Brook , Stony Brook, New York 11794-3400, United States.
authors.forename: Lisa
authors.initials: L
authors.lastname: Shah
authors.affiliation: Department of Chemistry and ‡Institute of Chemical Biology and Drug Discovery, State University of New York Stony Brook , Stony Brook, New York 11794-3400, United States.
authors.forename: Scott T
authors.initials: ST
authors.lastname: Laughlin
authors.affiliation: Department of Chemistry and ‡Institute of Chemical Biology and Drug Discovery, State University of New York Stony Brook , Stony Brook, New York 11794-3400, United States.
authors.forename: Isaac S
authors.initials: IS
authors.lastname: Carrico
mesh_terms: D000818:Animals; D001386:Azides / Q000737:chemistry / Q000378:metabolism; D004625:Embryo, Nonmammalian; D005452:Fluoresceins / Q000737:chemistry; D057809:HEK293 Cells; D006595:Hexosamines / Q000378:metabolism; D006801:Humans; D008856:Microscopy, Fluorescence; D057054:Molecular Imaging / Q000379:methods*; D010720:Phosphines / Q000737:chemistry*; D010777:Photochemistry / Q000379:methods*; D014466:Ultraviolet Rays; D015027:Zebrafish / Q000196:embryology
chemical_list: D001386:Azides; D005452:Fluoresceins; D006595:Hexosamines; C405953:N-azidoacetylmannosamine; D010720:Phosphines; C044646:phosphine