Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 34, Pages 11486-11493Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja803086r
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Funding
- National Institutes of Health [GM058867]
- Amgen Foundation
- National Science Foundation
- National Defense Science and Engineering
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The 1,3-dipolar cycloaddition of azides and activated alkynes has been used for site-selective labeling of biomolecules in vitro and in vivo. While copper catalysis has been widely employed to activate terminal alkynes for [3 + 2] cycloaddition, this method, often termed click chemistry, is currently incompatible with living systems because of the toxicity of the metal. We recently reported a difluorinated cyclooctyne (DIFO) reagent that rapidly reacts with azides in living cells without the need for copper catalysis. Here we report a novel class of DIFO reagents for copper-free click chemistry that are considerably more synthetically tractable. The new analogues maintained the same elevated rates of [3 + 2] cycloaddition as the parent compound and were used for imaging glycans on live cells. These second-gene ration DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists.
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