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. 2016 May 3;17(9):811-5.
doi: 10.1002/cbic.201600003. Epub 2016 Mar 31.

One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation

Takuya Machida  1 , Nicolas Winssinger  2
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One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation

Takuya Machida et al. Chembiochem. .

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.

Keywords: CuAAC; bioconjugation; carbohydrates; click chemistry; glycoconjugates.

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