Selective Deprotonated Amide Activation of Dehydroalanine for Peptide Modification
Abstract
Herein, we have discovered a unique deprotonated amide activation of dehydroalanine and developed a remote functionalization reaction of the double bond under mild conditions. The reaction exhibits good chemoselectivity and site-selectivity and is compatible with different kinds of peptides. Mechanistic studies first disclose in situ generated electron-rich enamine after deprotonation of amide hydrogen in Dha, followed by an intermolecular charge transfer process between the enamine and diaryliodonium salt.
Fields of Study & Subjects
Advanced Synthetic Organic Chemistry
Chemical Synthesis and Analysis
Coordination Chemistry and Organometallics
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 9
- Pages
- 2889–2894
- Publication date
- 19 February 2026
- Language
- EN