Triisobutylaluminium-Mediated Regioselective Protection of Sterically Hindered Amide NH of Cyclo-(AA-Gly): Key Building Block for Next-Generation Peptide Synthesis.

This article discusses the importance of peptides in various scientific disciplines and their growing demand in medicine. It explores new strategies, such as metal-mediated amidation, to improve the efficiency of peptide synthesis. The article focuses on the synthesis of mono-Boc-DKPs, a key building block for peptide synthesis, and the development of a regioselective protection method using trialkylaluminum. The authors conducted experiments to optimize the reaction conditions and found that the use of trialkylaluminum in combination with silicon reagents yielded the desired results. This method offers practical simplicity, scalability, and broad functional group tolerance, and it has the potential to facilitate the synthesis of regioselective mono-amide-NH-protected DKPs incorporating two amino acids with differing alkyl side chains. [Extracted from the article]