title: One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation.
abstract: We report a new reagent for the functionalization of unprotected oligosaccharides with a picolyl azide group at the anomeric position for chelation-assisted copper-catalyzed alkyne-azide cycloaddition (CuAAC) glycoconjugation. We show that oligosaccharides functionalized with this moiety react with an apparent second-order rate constant of 193 m(-1)  s(-1) and can be used to functionalize biomolecules bearing alkyne moieties introduced through metabolic labeling, including in live cells.
authors: Department of Organic Chemistry, NCCR Chemical Biology, University of Geneva, 30 quai Ernest Ansermet, 1211, Geneva, Switzerland.
authors: Takuya
authors: T
authors: Machida
authors: Department of Organic Chemistry, NCCR Chemical Biology, University of Geneva, 30 quai Ernest Ansermet, 1211, Geneva, Switzerland. nicolas.winssinger@unige.ch.
authors: Nicolas
authors: 0000-0003-1636-7766
authors: N
authors: Winssinger
mesh_terms: D000480:Alkynes / Q000737:chemistry / Q000378:metabolism; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D006367:HeLa Cells; D006801:Humans; D008856:Microscopy, Fluorescence; D009844:Oligosaccharides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D005456:Fluorescent Dyes; D006001:Glycoconjugates; D009844:Oligosaccharides; D010455:Peptides; C551041:homopropargylglycine; D003300:Copper; D004247:DNA; D005998:Glycine
keywords: CuAAC; bioconjugation; carbohydrates; click chemistry; glycoconjugates