期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 47, 页码 16893-16899出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja106553e
关键词
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资金
- National Institutes of Health [GM080585, T32 GM007491]
- Mizutani Foundation for Glycoscience
- Albert Einstein College of Medicine
- Office of Science, Office of Basic Energy Sciences, U.S. Department of Energy [DE-AC02-05 CH11231]
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.
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