A new method for peptide synthesis in the N→C direction: amide assembly through silver-promoted reaction of thioamides.
The Ag(I)-promoted coupling of amino acids and peptides with amino ester thioamides generates peptide imides without epimerisation. The peptide imides undergo regioselective hydrolysis under mild conditions to generate native peptides. This method was employed to prepare the pentapeptide thymopentin in the N→C direction, in high yield and purity.
School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, VIC 3010, Australia. chutton@unimelb.edu.au.
Aysa
A
Pourvali
James R
JR
Cochrane
Craig A
CA
Hutton
D006868:Hydrolysis; D007094:Imides / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*; D016305:Thymopentin / Q000138:chemical synthesis / Q000737:chemistry
D007094:Imides; D010455:Peptides; D013854:Thioamides; D012834:Silver; D016305:Thymopentin