N-acyl substituted 7-amino-4-chloroisocoumarin: a peptide degradation model via an imide mechanism.
During the coupling reaction between 3-alkoxy-7-amino-4-chloroisocoumarin and N-acyl alanine dipeptide, an unexpected deamidation reaction was observed. The proposed mechanism for this reaction involved the formation of an imide intermediate which after cleavage led to the release of amino acid moiety. The described deamidation reaction represents the first chemical model involving a non-peptidic moiety, which mimics biological and chemical deamidation processes occurring in proteins or peptides incorporating an asparagine or a glutamine residue.
Garino
Cédrik
C
INSERM U-382, Institut de Biologie du Développement de Marseille, CNRS-INSERM-Université de la Méditerranée, Faculté des Sciences de Luminy, case 907, 13288 Marseille Cedex 09, France.
Bihel
Frédéric
F
Souard
Florence
F
Quéléver
Gilles
G
Kraus
Jean-Louis
JL
D003374:Coumarins / Q000737:chemistry / Q000378:metabolism*; D007094:Imides / Q000737:chemistry / Q000378:metabolism*; D010455:Peptides / Q000737:chemistry / Q000378:metabolism*
D003374:Coumarins; D007094:Imides; D010455:Peptides