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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Mechanistic insights into Cu(I)-catalyzed azide-alkyne "click" cycloaddition monitored by real time infrared
1The Key Laboratory of Molecular Engineering of Polymers, Ministry of Education, Department of Macromolecular Science, and Laboratory of Advanced Materials, Fudan University, Shanghai 200433, People's Republic of China.
Abstract:
A designed ligand-accelerated Cu(I)-catalyzed cycloaddition (CuAAC) reaction was monitored for the first time by real time infrared analysis technique based on ATR-FTIR principles. Principal components analysis (PCA) and two-dimensional correlation spectroscopy (2Dcos) results showed that the consumption of alkyne and azide took place successively followed by the formation of the product 1,2,3-triazole, and a 1:1 complex of two reactants would be formed in the reaction process. The rate-determining step of the CuAAC reaction was also experimentally confirmed for the first time to be the transition of azide-alkyne 1:1 complex to the preproduct 1,2,3-triazole. Our results are in good conformity with the current catalytic mechanism proposed by Sharpless et al. according to DFT calculation results.
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