1047997-48-7Relevant academic research and scientific papers
Second-generation difluorinated cyclooctynes for copper-free click chemistry
Codelli, Julian A.,Baskin, Jeremy M.,Agard, Nicholas J.,Bertozzi, Carolyn R.
, p. 11486 - 11493 (2008)
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-generation DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists. ? 2008 American Chemical Society.
