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Enolization and racemization reactions of glucose and fructose on heating with amino-acid enantiomers and the formation of melanoidins as a result of the Maillard reaction

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Abstract

This study investigated the enolization and racemization reactions of glucose and fructose on heating with amino acid enantiomers and the formation of melanoidins as a result of the Maillard reaction. The study measured reducing sugars and L- and D- amino acids using HPLC as an index for the amount of enolization of the sugars and isomerization of the amino acids. Additionally, the absorption of melanoidins was measured at different wavelengths (420, 450, 470, 490 nm); the UV–Vis spectra and the extinction coefficient were determined for the formation of melanoidins. Melanoidins were, rather arbitrarily, defined by a high-molecular-weight (HMW) if it was above a lower limit of 12.4 kDa, which was the nominal cut-off value in the dialysis system used. A remarkable enolization reaction of the sugars was observed in the course of the Maillard reaction. Especially, in the Fru/D-Asn model system, the degree of sugar enolization was more than in the other model systems. All of the FDAA (1-fluoro-2, 4-dinitrophenyl-5-L-alanine amide) amino acids were separated by TLC. The racemization of the amino acids was higher in the fructose-amino acids systems. Isomer formation was the highest in the Fru/D-Asn system. The L- and D- isomers showed different absorptions in the UV–Vis spectra, although these had similar shapes. The absorption of the melanoidins formed from glucose was higher than that formed from fructose. In particular, the sugar–asparagine system showed different characteristics according to the L- and D-isomers. The differences in the extinction coefficients of the melanoidins was significant (P < 0.05), except for the sugar–lysine system.

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Acknowledgments

This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD, Basic Research Promotion Fund) (KRF-2006-511-C00133)

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  1. Department of Food and Nutrition, Kyung-Hee University, 1 Hoegi-dong, Dongdaemun-gu, Seoul, 130-701, South Korea

    Ji-Sang Kim & Young-Soon Lee

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  1. Ji-Sang Kim
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Correspondence to Young-Soon Lee.

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Kim, JS., Lee, YS. Enolization and racemization reactions of glucose and fructose on heating with amino-acid enantiomers and the formation of melanoidins as a result of the Maillard reaction. Amino Acids 36, 465–474 (2009). https://doi.org/10.1007/s00726-008-0104-z

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