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One‐Step Derivatization of Reducing Oligosaccharides for Rapid and Live‐Cell‐Compatible Chelation‐Assisted CuAAC Conjugation
Author(s) -
Machida Takuya,
Winssinger Nicolas
Publication year - 2016
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201600003
Subject(s) - derivatization , cycloaddition , azide , chemistry , chelation , combinatorial chemistry , alkyne , moiety , click chemistry , bioorthogonal chemistry , surface modification , reagent , anomer , organic chemistry , catalysis , high performance liquid chromatography
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.