Acrylamide and pyrazine formation in model systems containing asparagine.
The effect of different sugars and glyoxal on the formation of acrylamide in low-moisture starch-based model systems was studied, and kinetic data were obtained. Glucose was more effective than fructose, tagatose, or maltose in acrylamide formation, whereas the importance of glyoxal as a key sugar fragmentation intermediate was confirmed. Glyoxal formation was greater in model systems containing asparagine and glucose rather than fructose. A solid phase microextraction GC-MS method was employed to determine quantitatively the formation of pyrazines in model reaction systems. Substituted pyrazine formation was more evident in model systems containing fructose; however, the unsubstituted homologue, which was the only pyrazine identified in the headspace of glyoxal-asparagine systems, was formed at higher yields when aldoses were used as the reducing sugar. Highly significant correlations were obtained for the relationship between pyrazine and acrylamide formation. The importance of the tautomerization of the asparagine-carbonyl decarboxylated Schiff base in the relative yields of pyrazines and acrylamide is discussed.
Koutsidis
Georgios
G
Procter Department of Food Science, University of Leeds, Leeds LS2 9JT, United Kingdom. g.koutsidis@leeds.ac.uk
De la Fuente
Ana
A
Dimitriou
Chrisa
C
Kakoulli
Antonia
A
Wedzicha
Bronislaw L
BL
Mottram
Donald S
DS
D020106:Acrylamide / Q000138:chemical synthesis*; D001216:Asparagine / Q000737:chemistry*; D005632:Fructose / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006037:Glyoxal / Q000737:chemistry; D006358:Hot Temperature; D015416:Maillard Reaction; D008956:Models, Chemical; D011719:Pyrazines / Q000138:chemical synthesis*; D012545:Schiff Bases / Q000737:chemistry
D011719:Pyrazines; D012545:Schiff Bases; D020106:Acrylamide; D005632:Fructose; D006037:Glyoxal; D001216:Asparagine