Reactivity of biarylazacyclooctynones in copper-free click chemistry.

Journal of the American Chemical Society
Chelsea G GordonCarolyn R Bertozzi

Abstract

The 1,3-dipolar cycloaddition of cyclooctynes with azides, also called "copper-free click chemistry", is a bioorthogonal reaction with widespread applications in biological discovery. The kinetics of this reaction are of paramount importance for studies of dynamic processes, particularly in living subjects. Here we performed a systematic analysis of the effects of strain and electronics on the reactivity of cyclooctynes with azides through both experimental measurements and computational studies using a density functional theory (DFT) distortion/interaction transition state model. In particular, we focused on biarylazacyclooctynone (BARAC) because it reacts with azides faster than any other reported cyclooctyne and its modular synthesis facilitated rapid access to analogues. We found that substituents on BARAC's aryl rings can alter the calculated transition state interaction energy of the cycloaddition through electronic effects or the calculated distortion energy through steric effects. Experimental data confirmed that electronic perturbation of BARAC's aryl rings has a modest effect on reaction rate, whereas steric hindrance in the transition state can significantly retard the reaction. Drawing on these results, we analyzed ...Continue Reading

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Citations

Aug 25, 2012·Journal of the American Chemical Society·Rajesh Chakrabarty, Peter J Stang
Oct 26, 2012·Journal of the American Chemical Society·Frédéric FriscourtGeert-Jan Boons
Oct 16, 2012·Journal of the American Chemical Society·Yong LiangK N Houk
Sep 5, 2013·Journal of the American Chemical Society·David N KamberJennifer A Prescher
Jun 6, 2013·Organic Letters·Gabriela de AlmeidaCarolyn R Bertozzi
Jul 18, 2012·Chemical Communications : Chem Comm·Pamela V Chang, Carolyn R Bertozzi
Jan 18, 2014·ACS Chemical Biology·Kathrin Lang, Jason W Chin
Feb 13, 2014·Chemical Communications : Chem Comm·Xiaoshan Shayna WangWenshe R Liu
Jan 21, 2014·ACS Chemical Biology·David M PattersonJennifer A Prescher
Feb 5, 2014·Chemical Society Reviews·Benjamin Schulze, Ulrich S Schubert
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Mar 25, 2014·Chemical Reviews·Kathrin Lang, Jason W Chin
May 27, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mathieu ArseneaultJean-François Morin
Feb 9, 2016·Journal of the American Chemical Society·Joyann S BarberNeil K Garg
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Methods Mentioned

BETA
X-ray
electron diffraction

Software Mentioned

MOFO
DIMAC

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