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Biocompatible copper(I) catalysts for in vivo imaging of glycans.


ABSTRACT: The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is the standard method for bioorthogonal conjugation. However, current Cu(I) catalyst formulations are toxic, hindering their use in living systems. Here we report that BTTES, a tris(triazolylmethyl)amine-based ligand for Cu(I), promotes the cycloaddition reaction rapidly in living systems without apparent toxicity. This catalyst allows, for the first time, noninvasive imaging of fucosylated glycans during zebrafish early embryogenesis. We microinjected embryos with alkyne-bearing GDP-fucose at the one-cell stage and detected the metabolically incorporated unnatural sugars using the biocompatible click chemistry. Labeled glycans could be imaged in the enveloping layer of zebrafish embryos between blastula and early larval stages. This new method paves the way for rapid, noninvasive imaging of biomolecules in living organisms.

SUBMITTER: Soriano Del Amo D 

PROVIDER: S-EPMC3021957 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Biocompatible copper(I) catalysts for in vivo imaging of glycans.

Soriano Del Amo David D   Wang Wei W   Jiang Hao H   Besanceney Christen C   Yan Amy C AC   Levy Matthew M   Liu Yi Y   Marlow Florence L FL   Wu Peng P  

Journal of the American Chemical Society 20101109 47


The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is the standard method for bioorthogonal conjugation. However, current Cu(I) catalyst formulations are toxic, hindering their use in living systems. Here we report that BTTES, a tris(triazolylmethyl)amine-based ligand for Cu(I), promotes the cycloaddition reaction rapidly in living systems without apparent toxicity. This catalyst allows, for the first time, noninvasive imaging of fucosylated glycans during zebrafish early embryogenesis. We m  ...[more]

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