Amine capture strategy for peptide bond formation by means of quinolinium thioester salts.
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).
Leleu
Stéphane
S
Laboratoire de Chimie Organique Fine et Hétérocyclique UMR 6014 IRCOF, CNRS, Université et INSA de Rouen, B.P 08, F-76131 Mont-Saint-Aignan Cédex, France.
Penhoat
Maël
M
Bouet
Alexis
A
Dupas
Georges
G
Papamicaël
Cyril
C
Marsais
Francis
F
Levacher
Vincent
V
D000588:Amines / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*; D011806:Quinolinium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013463:Sulfuric Acid Esters / Q000737:chemistry*
D000588:Amines; D010455:Peptides; D011806:Quinolinium Compounds; D012492:Salts; D013463:Sulfuric Acid Esters