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J Am Chem Soc. 2010 Dec 1;132(47):16893-9. doi: 10.1021/ja106553e. Epub 2010 Nov 9.

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

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  • 1Department of Biochemistry, Albert Einstein College of Medicine, Yeshiva University, 1300 Morris Park Ave, Bronx, New York 10461, United States.

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.

PMID:
21062072
[PubMed - indexed for MEDLINE]
PMCID:
PMC3021957
Free PMC Article

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