Mechanistic pathways of formation of acrylamide from different amino acids.
Studies on model systems of amino acids and sugars have indicated that acrylamide can be generated from asparagine or from amino acids that can produce acrylic acid either directly such as beta-alanine, aspartic acid and carnosine or indirectly such as cysteine and serine. The main pathway specifically involves asparagine and produces acrylamide directly after a sugar-assisted decarboxylation and 1,2-elimination steps and the second non-specific pathway involves the initial formation of acrylic acid from different sources and its subsequent interaction with ammonia to produce acrylamide. Aspartic acid, beta-alanine and carnosine were found to follow acrylic acid pathway. Labeling studies with [13C-4]aspartic acid have confirmed the occurrence in aspartic acid model system, of a previously proposed sugar-assisted decarboxylation mechanism identified in asparagine model systems. In addition, creatine was found to be a good source of methylamine and was responsible for the formation of N-methylacrylamide in model systems through acrylic acid pathway. Furthermore, certain amino acids such as serine and cysteine were found to generate pyruvic acid that can be converted into acrylic acid and generate acrylamide when reacted with ammonia.
Yaylayan
Varoujan A
VA
McGill University, Department of Food Science and Agricultural Chemistry, 21, 111 Lakeshore, Ste. Anne de Bellevue, Quebec, Canada H9X 3V9. varoujan.yaylayan@mcgill.ca
Locas
Carolina Perez
CP
Wnorowski
Andrzej
A
O'Brien
John
J
D020106:Acrylamide / Q000032:analysis / Q000737:chemistry*; D000178:Acrylamides / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D000641:Ammonia / Q000737:chemistry; D001216:Asparagine / Q000737:chemistry; D001224:Aspartic Acid / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D002336:Carnosine / Q000737:chemistry; D003401:Creatine / Q000737:chemistry; D003545:Cysteine / Q000737:chemistry; D005632:Fructose / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D013058:Mass Spectrometry; D008956:Models, Chemical; D019289:Pyruvic Acid / Q000737:chemistry; D012694:Serine / Q000737:chemistry; D013997:Time Factors; D015091:beta-Alanine / Q000737:chemistry
D000178:Acrylamides; D000179:Acrylates; D000596:Amino Acids; D002241:Carbohydrates; D015091:beta-Alanine; D020106:Acrylamide; D005632:Fructose; D001224:Aspartic Acid; D012694:Serine; C491267:N-methylacrylamide; D001216:Asparagine; D000641:Ammonia; D019289:Pyruvic Acid; D002336:Carnosine; C036658:acrylic acid; D003545:Cysteine; D003401:Creatine