3-Methyl-2(1H)-pyrazinones, the Asparagine-Specific Maillard Products Formed from Asparagine and Monosaccharides

Shu, Chi-Kuen; Lawrence, Brian M.

doi:10.1021/jf00051a040

Cited by 12 publications

(25 citation statements)

References 8 publications

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“…These results show that both reactions generated very similar compounds including various pyrazines, pyrroles, maleimides, and pyrazinones. Of those compounds identified, the two 2(1H)-pyrazinones have already been reported as asparagine-specific Maillard products (Shu and Lawrence, 1995) and the formation of the two maleimides appears to originate from asparagine alone (Wilken and Baltes, 1990).…”

Section: Resultsmentioning

confidence: 99%

Flavor Components Generated from Inulin

Shu

1998

J. Agric. Food Chem.

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Inulin is a linear oligmer of 2f1-linked β-D-fructose ending in an R-D-glucose unit, as a nonreducing sugar. The objective of this study was to investigate the reactions between inulin and asparagine as well as those between inulin and diammonium hydrogen phosphate (an ammonia precursor) using model systems at 200 °C in water. The flavor components formed from these reactions were found to be similar to those obtained from the corresponding reactions with fructose. It is implied that inulin may chemically function as fructose under these conditions. Further experiments showed that inulin started to be depolymerized into fructose in aqueous solution at 150 °C. As a result, this study demonstrates that although inulin cannot directly react with nitrogen-containing compounds to participate in Maillard reactions, it can do so indirectly after it is depolymerized into fructose. These finding suggests that inulin may be used as a fructose precursor in wet food systems.

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Section: Resultsmentioning

confidence: 99%

Flavor Components Generated from Inulin

Shu

1998

J. Agric. Food Chem.

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“…With respect to the intermediate stages of the Maillard reaction, volatile compounds such as furans, pyrans, and pyrroles have been obtained in larger amounts from fructose than from glucose when each sugar was heated in the presence of â-alanine (Nishibori and Bernhard 1993). Other products with the nitrogen atoms from amino acids, such as pyrazines (Amrani-Hemaimi and others 1995), as well as more specific products from asparagine (Shu and Lawrence 1995) were apparently formed irrespective of the nature of the reducing sugar. Some mechanistic differences seem very likely to exist between the nonenzymatic browning reaction of fructose and that of glucose as suggested, for example, by the existence of a lag time in the browning of glucose solutions and not in that of fructose solutions (Kato and others 1969;Buera and others 1987;Ajandouz and Puigserver 1999).…”

Section: Final Stagesmentioning

confidence: 98%

Effects of pH on Caramelization and Maillard Reaction Kinetics in Fructose‐Lysine Model Systems

Ajandouz

Tchiakpe

Ore

et al. 2001

Journal of Food Science

431

305

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The nonenzymatic browning reactions of fructose and fructose-lysine aqueous model systems were investigated at 100 Њ Њ Њ Њ ЊC between pH 4.0 and pH 12.0 by measuring the loss of reactants and monitoring the pattern of UV-absorbance and brown color development. At all the pH values tested, the loss of fructose was lower in the presence than in the absence of lysine. And, in lysine-containing fructose solution, the sugar disappeared more rapidly than the amino acid. Lysine was moderately lost below pH 8.0. Caramelization of fructose, which accounted for more than 40% of total UV-absorbance and 10 to 36% of brown color development, may therefore lead to overestimating the Maillard reaction in foods.

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“…14), or the condensation of a-dicarbonyl with isoasparagine. 46 Model systems of Gly-Leu and Leu-Gly with MGO were also studied. It was found that a peptide sequence did not affect the type of aromas, but only changed the amount of pyrazinones slightly.…”

Section: Formation Of Pyrazinones From Peptides and Alphadicarbonylsmentioning

confidence: 99%

Flavour chemistry of methylglyoxal and glyoxal

2012

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Methylglyoxal (MGO) and glyoxal (GO), known as reactive carbonyl species, can be generated endogenously and exogenously (human body and food system). They are attracting increased attention because of their relationship with diabetes and flavour generation. In this review, their characteristics relating to flavour chemistry are discussed. MGO and GO can be detected in food systems by GC and HPLC after derivatization. MGO and GO formed in the Maillard reaction play important roles as precursors of aroma and colour compounds, especially in Strecker degradation, a major flavour generation reaction. When combined with amino acids they undergo Schiff base formation, decarboxylation and α-aminoketone condensation leading to heterocyclic aroma compounds such as pyrazines, pyrroles and pyridines. They attack amine groups in amino acids, peptides and proteins to form advanced glycation end products (AGEs) and cause carbonyl stress followed by oxidative stress and tissue damage. Therefore, many studies about scavengers of MGO and GO are seen. The influence of these scavengers on flavour generation is also discussed.

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3-Methyl-2(1H)-pyrazinones, the Asparagine-Specific Maillard Products Formed from Asparagine and Monosaccharides

Cited by 12 publications

References 8 publications

Flavor Components Generated from Inulin

Flavor Components Generated from Inulin

Effects of pH on Caramelization and Maillard Reaction Kinetics in Fructose‐Lysine Model Systems

Flavour chemistry of methylglyoxal and glyoxal

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