Why asparagine needs carbohydrates to generate acrylamide.
Structural considerations dictate that asparagine alone may be converted thermally into acrylamide through decarboxylation and deamination reactions. However, the main product of the thermal decomposition of asparagine was maleimide, mainly due to the fast intramolecular cyclization reaction that prevents the formation of acrylamide. On the other hand, asparagine, in the presence of reducing sugars, was able to generate acrylamide in addition to maleimide. Model reactions were performed using FTIR analysis, and labeling studies were carried out using pyrolysis-GC/MS as an integrated reaction, separation, and identification system to investigate the role of reducing sugars. The data have indicated that a decarboxylated Amadori product of asparagine with reducing sugars is the key precursor of acrylamide. Furthermore, the decarboxylated Amadori product can be formed under mild conditions through the intramolecular cyclization of the initial Schiff base and formation of oxazolidin-5-one. The low-energy decarboxylation of this intermediate makes it possible to bypass the cyclization reaction, which is in competition with thermally induced decarboxylation, and hence promote the formation of acrylamide in carbohydrate/asparagine mixtures. Although the decarboxylated Amadori compound can be formed under mild conditions, it requires elevated temperatures to cleave the carbon-nitrogen covalent bond and produce acrylamide.
Yaylayan
Varoujan A
VA
Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec, Canada H9X 3V9. varoujan.yaylayan@mcgill.ca
Wnorowski
Andrzej
A
Perez Locas
Carolina
C
D020106:Acrylamide / Q000737:chemistry*; D001216:Asparagine / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D003653:Decarboxylation; D008401:Gas Chromatography-Mass Spectrometry; D006358:Hot Temperature; D008301:Maleimides / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
D002241:Carbohydrates; D008301:Maleimides; D020106:Acrylamide; C043592:maleimide; D001216:Asparagine