Amine Capture Strategy for Peptide Bond Formation by Means of Quinolinium Thioester Salts

• Published in: Journal of the American Chemical Society Vol. 127; no. 45; pp. 15668 - 15669
• Main Authors: Leleu, Stéphane, Penhoat, Maël, Bouet, Alexis, Dupas, Georges, Papamicaël, Cyril, Marsais, Francis, Levacher, Vincent
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.11.2005; Amer Chemical Soc
• Subjects: Amines - chemistry; Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Organic chemistry; Peptides; Peptides - chemical synthesis; Physical Sciences; Preparations and properties; Quinolinium Compounds - chemistry; Salts - chemistry; Science & Technology; Sulfuric Acid Esters - chemistry; LIGATION; SAFETY-CATCH LINKER; TRANSFERRING AGENTS; CHEMICAL-SYNTHESIS; PROTEIN; SOLID SUPPORT; Organic synthesis; Aminoester; Peptide bond; Thioester; Tertiary amine; Peptide synthesis; Primary amine; Chemical coupling; Ultraviolet visible spectrometry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja054775p

A new and unprecedented exploitation of quinolinium thioester salts 2 in peptide bond formation is reported. These synthetic tools were assessed during the preparation of a number of dipeptides 3a−f obtained in good yields with complete stereochemical integrity. A sequential mechanism related to a prior amine capture strategy is well-established. Additionally, a tripeptide 3g was prepared according to a “safety-catch” approach, thus demonstrating the important potential of these new synthetic tools in the design of new safety-catch linkers exploitable in Solid-Phase Peptide Synthesis (SPPS).