title: N-acyl substituted 7-amino-4-chloroisocoumarin: a peptide degradation model via an imide mechanism.
abstract: 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.
authors.affiliation: 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.
authors.forename: Cédrik
authors.initials: C
authors.lastname: Garino
authors.forename: Frédéric
authors.initials: F
authors.lastname: Bihel
authors.forename: Florence
authors.initials: F
authors.lastname: Souard
authors.forename: Gilles
authors.initials: G
authors.lastname: Quéléver
authors.forename: Jean-Louis
authors.initials: JL
authors.lastname: Kraus
mesh_terms: D003374:Coumarins / Q000737:chemistry / Q000378:metabolism*; D007094:Imides / Q000737:chemistry / Q000378:metabolism*; D010455:Peptides / Q000737:chemistry / Q000378:metabolism*
chemical_list: D003374:Coumarins; D007094:Imides; D010455:Peptides