The role of creatine in the generation of N-methylacrylamide: a new toxicant in cooked meat.
Investigations of different sources of acrylamide formation in model systems consisting of amino acids and sugars have indicated the presence of two pathways of acrylamide generation; the main pathway specifically involves asparagine to directly produce acrylamide after a sugar-assisted decarboxylation step, and the second, nonspecific pathway involves the initial formation of acrylic acid from different sources and its subsequent interaction with ammonia and/or amines to produce acrylamide or its N-alkylated derivatives. Aspartic acid, beta-alanine, and carnosine were found to follow the acrylic acid pathway. Labeling studies using [(13)C-4]aspartic acid have confirmed the occurrence in this amino acid of a previously proposed sugar-assisted decarboxylation mechanism identified in the asparagine/glucose model system. In addition, creatine was found to be a good source of methylamine in model systems and was responsible for the formation of N-methylacrylamide through the acrylic acid pathway. Labeling studies using creatine (methyl-d(3)) and (15)NH(4)Cl have indicated that both the nitrogen and the methyl groups of methylamine had originated from creatine. Furthermore, analysis of cooked meat samples has also confirmed the formation of N-methylacrylamide during cooking.
Department of Food Science and Agricultural Chemistry, McGill University, 21111 Lakeshore, Ste. Anne de Bellevue, Quebec H9X 3V9, Canada. varoujan.yaylayan@mcgill.ca
Varoujan A
VA
Yaylayan
Carolina Perez
CP
Locas
Andrzej
A
Wnorowski
John
J
O'Brien
D020106:Acrylamide / Q000737:chemistry; D000178:Acrylamides / Q000737:chemistry*; D000179:Acrylates / Q000737:chemistry; D001224:Aspartic Acid / Q000737:chemistry; D002336:Carnosine / Q000737:chemistry; D003401:Creatine / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D006358:Hot Temperature; D013058:Mass Spectrometry; D008460:Meat / Q000032:analysis*; D008744:Methylamines / Q000737:chemistry; D015091:beta-Alanine / Q000737:chemistry
D000178:Acrylamides; D000179:Acrylates; D008744:Methylamines; D015091:beta-Alanine; D020106:Acrylamide; D001224:Aspartic Acid; C491267:N-methylacrylamide; D002336:Carnosine; C027451:methylamine; C036658:acrylic acid; D003401:Creatine