An Unexpected Example of Protein-Templated Click Chemistry

摘要

Click chemistry is a popular approach to the synthesis of functionalized molecules, and emphasizes the use of practical and reliable reactions. Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), which selectively produces anti-(1,4)-triazoles in preference to the syn isomer (1,5-triazole), is regarded as a superlative example of click chemistry. The CuAAC reaction can be accelerated by Cu~I-stabilizing ligands, such as tris[(1-substituted-1H,2,3-triazol-4-yl)me-thyl]amines and tris(2-benzimidazolylmethyl)amines. The catalytic system has received a great deal of use in various fields such as chemical biology and materials science. The 1,3-dipolar cycloaddition of azides with unactivated alkynes occurs much more slowly but is highly chemoselective.