title: Synthesis of cyclic peptides through direct aminolysis of peptide thioesters catalyzed by imidazole in aqueous organic solutions.
abstract: A promising method for the synthesis of cyclic peptides through the direct aminolysis of peptide thioesters is presented. The cyclization step was carried out in a mixture of acetonitrile and 1.5 M aqueous imidazole solution with no observable oligomers. Studies on the N- and C-terminal residues show that the choice of C-terminal residue has a more significant effect on the success rate of cyclization than the choice at the N-terminal residue.
authors.affiliation: Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port Saint Lucie, Florida 34987, USA.
authors.forename: Yangmei
authors.initials: Y
authors.lastname: Li
authors.forename: Austin
authors.initials: A
authors.lastname: Yongye
authors.forename: Marc
authors.initials: M
authors.lastname: Giulianotti
authors.forename: Karina
authors.initials: K
authors.lastname: Martinez-Mayorga
authors.forename: Yongping
authors.initials: Y
authors.lastname: Yu
authors.forename: Richard A
authors.initials: RA
authors.lastname: Houghten
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D000097:Acetonitriles; D004952:Esters; D007093:Imidazoles; D010456:Peptides, Cyclic; D012996:Solutions; D013438:Sulfhydryl Compounds; D014867:Water; C029899:imidazole; C032159:acetonitrile