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
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- PMID: 26852736
- DOI: 10.1002/cbic.201600003
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One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation
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.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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