Stereoselective Access to Azetidine-Based α-Amino Acids and Applications to Small Peptide Synthesis
Felix Reiners, Emanuel Joseph, Benedikt Nißl, Dorian Didier
Abstract
Non-natural azetidine-based amino acids (Aze) present interesting features in protein engineering. A simple organometallic route toward unsaturated carboxylic acid precursors is presented. Subsequent metal-catalyzed asymmetric reduction allowed for the synthesis of a new library of 2-azetidinylcarboxylic acids, which were finally employed in the formation of small peptide chains.
Topics & Concepts
ChemistryAzetidineAmino acidStereoselectivityPeptideCombinatorial chemistryCatalysisPeptide synthesisStereochemistryOrganic chemistryBiochemistrySynthesis and Catalytic ReactionsChemical Synthesis and AnalysisSynthesis of β-Lactam Compounds