Synthesis of cyclic peptides through direct aminolysis of peptide thioesters catalyzed by imidazole in aqueous organic solutions.
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.
Li
Yangmei
Y
Torrey Pines Institute for Molecular Studies, 11350 SW Village Parkway, Port Saint Lucie, Florida 34987, USA.
Yongye
Austin
A
Giulianotti
Marc
M
Martinez-Mayorga
Karina
K
Yu
Yongping
Y
Houghten
Richard A
RA
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
D000097:Acetonitriles; D004952:Esters; D007093:Imidazoles; D010456:Peptides, Cyclic; D012996:Solutions; D013438:Sulfhydryl Compounds; D014867:Water; C029899:imidazole; C032159:acetonitrile