title: A bioorthogonal ligation enabled by click cycloaddition of o-quinolinone quinone methide and vinyl thioether.
abstract: There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddition of in situ-generated o-quinolinone quinone methides and vinyl thioethers. This reaction is highly selective and proceeds smoothly under aqueous conditions. The functionalized vinyl thioethers are small and chemically stable in vivo, making them suitable for use as bioorthogonal chemical reporters that can be effectively coupled to various biomolecules. We utilized this bioorthogonal ligation for site-specific labeling of proteins as well as imaging of bioactive small molecules inside live cells.
authors.affiliation: Peking Union Medical College and Chinese Academy of Medical Sciences , Beijing 100730, China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Li
authors.forename: Ting
authors.initials: T
authors.lastname: Dong
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Liu
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Lei
mesh_terms: D019921:Biotinylation; D002463:Cell Membrane Permeability; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D019793:Fluorescein; D006367:HeLa Cells; D006801:Humans; D045563:Indolequinones / Q000737:chemistry*; D057054:Molecular Imaging; D015394:Molecular Structure; D017239:Paclitaxel / Q000737:chemistry; D015363:Quinolones / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D045563:Indolequinones; D015363:Quinolones; D013440:Sulfides; D014753:Vinyl Compounds; C068040:quinone methide; D017239:Paclitaxel; D019793:Fluorescein