Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation
Masayoshi Koshizuka, Kazuishi Makino, Naoyuki Shimada
Abstract
We report the catalytic direct peptide bond formations via dehydrative condensation of β-hydroxy-α-amino acids, affording the serine, threonine, or β-hydroxyvaline-derived peptides in high to excellent yields with high functional group tolerance, minimum epimerization, and excellent chemoselectivity. The key to the success of these atom-economical transformations is the use of diboronic acid anhydride catalyst for the hydroxy-directed reactions.
Topics & Concepts
ChemistryChemoselectivityCatalysisEpimerSerineCondensationCombinatorial chemistryThreonineOrganic chemistryBrønsted–Lowry acid–base theoryAmino acidPeptideMedicinal chemistryBiochemistryThermodynamicsPhysicsEnzymeChemical Synthesis and AnalysisPeptidase Inhibition and AnalysisClick Chemistry and Applications