A new method for peptide synthesis in the N arrow right C direction: amide assembly through silver-promoted reaction of thioamides

A new method for peptide synthesis in the N arrow right 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...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2014-11, Vol.50 (100), p.15963-15966
Hauptverfasser: Pourvali, Aysa, Cochrane, James R, Hutton, Craig A
Format: Artikel
Sprache:eng
Schlagworte:
Amides
Amino acids
Assembly
Coupling
Esters
Hydrolysis
Imides
Peptides
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Beschreibung
Zusammenfassung: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 arrow right C direction, in high yield and purity.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc07601j