CHEM Talks: Nobel Laureate Professor Morten Meldal
“A Nobel tour of Chemistry: The ∆S driven intramolecular INAIC click? reaction”
The Nobel tour and the CuAAC click reaction1 will be briefly presented with mechanistic considerations and some of our applications. The INAIC – reaction which in many respects follow click criteria will be presented. The INAIC reaction was discovered by NMR- investigations of peptide aldehydes showing entropy driven quantitative and highly selective reaction with backbone or sidechain amides in the peptide to form reactive N-acyl iminium ions, which in turn react with C, O, N or S nucleophiles in the peptide to form multiple heterocycles in a stereo and enantioselective manner.2 Many examples of this versatile reaction will be presented.
- Tornøe, C. W., & Meldal, M. (2001). Peptidotriazoles: Copper (I)-catalyzed 1, 3-dipolar cycloadditions on solid-phase. In Peptides: The Wave of the Future: Proceedings of the Second International and the Seventeenth American Peptide Symposium, June 9–14, 2001, San Diego, California, USA (pp. 263-264).
- Nielsen, T. E., & Meldal, M. (2004). Solid-phase intramolecular N-acyliminium Pictet− Spengler reactions as crossroads to scaffold diversity. The Journal of Organic Chemistry, 69(11), 3765-3773.