Chemistry of Nonenzymic Browning I. The Reaction between Aldoses and Amines

Reynolds, T. M.

doi:10.1016/s0065-2628(08)60005-1

Cited by 253 publications

(73 citation statements)

References 103 publications

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“…This finding was thought to be a possible mechanism for accelerated atherogenesis in diabetes (17,18). To examine whether O 2 . was also generated in this model reaction, we performed NBT reduction experiments by adding varying concentrations of the reaction mixture.…”

Section: Effects Of Molecular Oxygens and Metal Ions-mentioning

confidence: 99%

“…These results demonstrate that although the initiation of the cross-linking reaction does not require molecular oxygen, the reaction products generate superoxide radical anions in the presence of oxygen. The methylglyoxal radical anion is most likely responsible for O 2 . generation by its electron transfer reaction to oxygen via Reaction 2.…”

Section: Effects Of Molecular Oxygens and Metal Ions-mentioning

confidence: 99%

“…This process is initiated by the condensation reaction of reducing sugars with free amino groups to form Schiff bases (Fig. 1A), which undergo rearrangement to form the relatively stable Amadori products (2,3). The Amadori products subsequently degrade into ␣-dicarbonyl compounds, deoxyglucosones (4,5).…”

mentioning

confidence: 99%

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Free Radicals Generated during the Glycation Reaction of Amino Acids by Methylglyoxal

Yim

Kang

Hah

et al. 1995

Journal of Biological Chemistry

237

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The formation of ␣-dicarbonyl compounds seems to be an important step for cross-linking proteins in the glycation or Maillard reaction. To elucidate the mechanism for the cross-linking reaction, we studied the reaction between a three-carbon ␣-dicarbonyl compound, methylglyoxal, and amino acids. Our results showed that this reaction generated yellow fluorescent products as formed in some glycated proteins. In addition, three types of free radical species were also produced, and their structures were determined by EPR spectroscopy. These free radicals are 1) the cross-linked radical cation, 2) the methylglyoxal radical anion as the counterion, and 3) the superoxide radical anion produced only in the presence of oxygen. The generation of the crosslinked radical cations and the methylglyoxal radical anions does not require metal ions or oxygens. These results indicate that dicarbonyl compounds cross-link free amino groups of protein by forming Schiff bases, which donate electrons directly to dicarbonyl compounds to form the cross-linked radical cations and the methylglyoxal radical anions. Oxygen can accept an electron from the radical anion to generate a superoxide radical anion, which can initiate damaging chain reactions. Time course studies suggest that the cross-linked radical cation is a precursor of yellow fluorescent glycation end products.

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Section: Effects Of Molecular Oxygens and Metal Ions-mentioning

confidence: 99%

Section: Effects Of Molecular Oxygens and Metal Ions-mentioning

confidence: 99%

See 1 more Smart Citation

Free Radicals Generated during the Glycation Reaction of Amino Acids by Methylglyoxal

Yim

Kang

Hah

et al. 1995

Journal of Biological Chemistry

237

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show abstract

“…Considering the striking morphological similarities of peanuts and cocoa beans (27) and the similarity of the roasting process to which each is subjected, it is not surprising that these two foods have the same flavo~ precursors (amino acids and carbohydrates). It is surprising that simple alkylated pyrazines have not been isolated from roasted cocoa beans since they have been characterized in peanuts (13), coffee (28,29) and heated carbol;lydrate-amino acid model systems (30,Chapter VI (33,34), Ellis (35), Anet (36) and Hodge (37). The very de.…”

Section: Peanut Flavor Componentsmentioning

confidence: 99%

“…The very de. tailed reviews of Reynolds (33,34) are an excellent guide for those interested in the preparation and properties of intermediates in the Mail-· lard reaction; the review of Hodge (37) give a reductone or a reductone-like product containing nitrogen in the case of dehydration of an oi,~-unsaturated aldimine.…”

Section: Peanut Flavor Componentsmentioning

confidence: 99%