Biocompatible Copper(I) Catalysts for in Vivo Imaging of Glycans

被引：305

作者：

del Amo, David Soriano ^{[1
]}

Wang, Wei ^{[1
]}

Jiang, Hao ^{[1
]}

Besanceney, Christen ^{[1
]}

Yan, Amy C. ^{[1
]}

Levy, Matthew ^{[1
]}

Liu, Yi ^{[2
]}

Marlow, Florence L.

Wu, Peng ^{[1
]}

机构：

[1] Yeshiva Univ, Albert Einstein Coll Med, Dept Biochem, Bronx, NY 10461 USA

[2] Univ Calif Berkeley, Lawrence Berkeley Lab, Mol Foundry, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 47期

基金：

美国国家卫生研究院;

关键词：

AZIDE-ALKYNE CYCLOADDITION; FREE CLICK CHEMISTRY; FUCOSYLATED GLYCANS; VISUALIZATION; LIGATION; FUCOSE;

D O I：

10.1021/ja106553e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：16893 / 16899

页数：7

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