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Volumn 47, Issue 2, 1999, Pages 379-390

Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids

Author keywords

1,4 Dialkylpyrazinium radical cation; Amadori product; Deoxyosones; Glycolaldehyde; Glyoxal; Maillard reaction; Nonenzymatic browning; Oxidation

Indexed keywords

ALANINE; ALDEHYDE; AMINO ACID; CARBOHYDRATE; FREE RADICAL; FURFURAL; HEXOSE; PYRAZINE DERIVATIVE; RADICAL;

EID: 0032968519     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980626x     Document Type: Article
Times cited : (128)

References (33)
  • 1
    • 0001296603 scopus 로고
    • Formation of 1-deoxy-D-erythro-2,3-hexodiulose from Amadori compounds
    • Beck, J.; Ledl, F.; Severin, Th. Formation of 1-deoxy-D-erythro-2,3-hexodiulose from Amadori compounds. Carbohydr. Res. 1988, 177, 240-243.
    • (1988) Carbohydr. Res. , vol.177 , pp. 240-243
    • Beck, J.1    Ledl, F.2    Severin, Th.3
  • 2
    • 0000875450 scopus 로고
    • Diquaternary salts. I. Preparation and characterization of the diquaternary salts of some diazines and diazoles
    • Curphey, T. J.; Prasad, K. S. Diquaternary salts. I. Preparation and characterization of the diquaternary salts of some diazines and diazoles. J. Org. Chem. 1972, 37, 2259-2265.
    • (1972) J. Org. Chem. , vol.37 , pp. 2259-2265
    • Curphey, T.J.1    Prasad, K.S.2
  • 4
    • 0028934990 scopus 로고
    • Mechanism of protein modification by glyoxal and glycolaldehyde, reactive intermediates of the Maillard reaction
    • Glomb, M. A.; Monnier, V. M. Mechanism of protein modification by glyoxal and glycolaldehyde, reactive intermediates of the Maillard reaction. J. Biol. Chem. 1995, 270, 10017-10026.
    • (1995) J. Biol. Chem. , vol.270 , pp. 10017-10026
    • Glomb, M.A.1    Monnier, V.M.2
  • 5
    • 0000727059 scopus 로고
    • Formation of two-carbon sugar fragment at an early stage of the browning reaction of sugar with amine
    • Hayashi, T.; Namiki, M. Formation of two-carbon sugar fragment at an early stage of the browning reaction of sugar with amine. Agric. Biol. Chem. 1980, 44, 2575-2580.
    • (1980) Agric. Biol. Chem. , vol.44 , pp. 2575-2580
    • Hayashi, T.1    Namiki, M.2
  • 6
    • 0017551258 scopus 로고
    • Electron spin resonance spectral study on the structure of the novel free radical products formed by the reactions of sugars with amino acids or amines
    • Hayashi, T.; Ohta, Y.; Namiki, M. Electron spin resonance spectral study on the structure of the novel free radical products formed by the reactions of sugars with amino acids or amines. J. Agric. Food Chem. 1977, 25, 1282-1287.
    • (1977) J. Agric. Food Chem. , vol.25 , pp. 1282-1287
    • Hayashi, T.1    Ohta, Y.2    Namiki, M.3
  • 7
    • 0001059165 scopus 로고
    • Formation of the N,N′-dialkylpyrazine cation radical from glyoxal dialkylimine produced on reaction of a sugar with an amine or amino acid
    • Hayashi, T.; Mase, S., Namiki, M. Formation of the N,N′-dialkylpyrazine cation radical from glyoxal dialkylimine produced on reaction of a sugar with an amine or amino acid. Agric. Biol. Chem. 1985, 49, 3131-3137.
    • (1985) Agric. Biol. Chem. , vol.49 , pp. 3131-3137
    • Hayashi, T.1    Mase, S.2    Namiki, M.3
  • 8
    • 33947448299 scopus 로고
    • Chemistry of browning reactions in model systems
    • Hodge, J. E. Chemistry of browning reactions in model systems. J. Agric. Food Chem. 1953, 1, 928-943.
    • (1953) J. Agric. Food Chem. , vol.1 , pp. 928-943
    • Hodge, J.E.1
  • 9
    • 0030760011 scopus 로고    scopus 로고
    • Determination of the chemical structure of novel colored 1H-pyrrol-3(2H)-one derivatives formed by Maillard-type reactions
    • Hofmann, T. Determination of the chemical structure of novel colored 1H-pyrrol-3(2H)-one derivatives formed by Maillard-type reactions. Helv. Chim. Acta 1997a, 80, 1843-1856.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 1843-1856
    • Hofmann, T.1
  • 10
    • 0345287963 scopus 로고    scopus 로고
    • Determination of the chemical structure of novel coloured compounds generated by Maillard-type reactions
    • O'Brien, J., Nursten, H. E., Crabbe, M. J. C., Ames, J. M., Eds.; Royal Society of Chemistry: Cambridge, U.K.
    • Hofmann, T. Determination of the chemical structure of novel coloured compounds generated by Maillard-type reactions. In Proceedings of the 6th International Symposium on the Maillard Reaction; O'Brien, J., Nursten, H. E., Crabbe, M. J. C., Ames, J. M., Eds.; Royal Society of Chemistry: Cambridge, U.K., 1997b; pp 82-88.
    • (1997) Proceedings of the 6th International Symposium on the Maillard Reaction , pp. 82-88
    • Hofmann, T.1
  • 11
    • 0000005543 scopus 로고    scopus 로고
    • Characterization of the chemical structure of novel colored Maillard reaction products from furan-2-carboxaldehyde and amino acids
    • Hofmann, T. Characterization of the chemical structure of novel colored Maillard reaction products from furan-2-carboxaldehyde and amino acids. J. Agric. Food Chem. 1998a, 46, 932-940.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 932-940
    • Hofmann, T.1
  • 12
    • 0032462519 scopus 로고    scopus 로고
    • Characterization of the most intense coloured compounds from Maillard reactions of pentoses by application of colour dilution analysis (CDA)
    • submitted for publication
    • Hofmann, T. Characterization of the most intense coloured compounds from Maillard reactions of pentoses by application of colour dilution analysis (CDA). Carbohydr. Res. 1998b, submitted for publication.
    • (1998) Carbohydr. Res.
    • Hofmann, T.1
  • 13
    • 0000219608 scopus 로고    scopus 로고
    • Identification of novel colored compounds containing pyrrole and pyrrolinone structures formed by Maillard reactions of pentoses and primary amino acids
    • Hofmann, T. Identification of novel colored compounds containing pyrrole and pyrrolinone structures formed by Maillard reactions of pentoses and primary amino acids. J. Agric. Food Chem. 1998c, 46, 3902-3911.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 3902-3911
    • Hofmann, T.1
  • 14
    • 0000334043 scopus 로고    scopus 로고
    • Acetylformoin - A chemical switch in the formation of colored Maillard reaction products from hexoses and primary and secondary amino acids
    • Hofmann, T. Acetylformoin - a chemical switch in the formation of colored Maillard reaction products from hexoses and primary and secondary amino acids. J. Agric. Food Chem. 1998d, 46, 3918-3928.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 3918-3928
    • Hofmann, T.1
  • 15
    • 0001489984 scopus 로고    scopus 로고
    • Studies on the relationship between the molecular weight and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentrifugation and color dilution techniques
    • Hofmann, T. Studies on the relationship between the molecular weight and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentrifugation and color dilution techniques. J. Agric. Food Chem. 1998e, 46, 3891-3895.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 3891-3895
    • Hofmann, T.1
  • 16
    • 0032469454 scopus 로고    scopus 로고
    • 13C-labeling experiments
    • submitted for publication
    • 13C-labeling experiments. Carbohydr. Res. 1998f, submitted for publication.
    • (1998) Carbohydr. Res.
    • Hofmann, T.1
  • 17
    • 0000752630 scopus 로고    scopus 로고
    • 13C NMR spectroscopy for the elucidation of the formation pathway leading to a red colored l1H-pyrrol-3(2H)-one during the Maillard reaction of furan-2-carboxaldehyde and L-alanine
    • 13C NMR spectroscopy for the elucidation of the formation pathway leading to a red colored l1H-pyrrol-3(2H)-one during the Maillard reaction of furan-2-carboxaldehyde and L-alanine. J. Agric. Food Chem. 1998g, 46, 941-945.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 941-945
    • Hofmann, T.1
  • 18
    • 0345287960 scopus 로고    scopus 로고
    • Determination of the contribution of coloured Maillard reaction products to the total colour of browned glucose/alanine solutions and studies on their formation
    • submitted for publication
    • Hofmann, T.; Heuberger, S. Determination of the contribution of coloured Maillard reaction products to the total colour of browned glucose/alanine solutions and studies on their formation. Z. Lebensm. Unters. Forsch. 1998, submitted for publication.
    • (1998) Z. Lebensm. Unters. Forsch.
    • Hofmann, T.1    Heuberger, S.2
  • 19
    • 0000753788 scopus 로고
    • Studies on the formation and stability of the roast-flavor compound 2-acetyl-2-thiazoline
    • Hofmann, T.; Schieberle, P. Studies on the formation and stability of the roast-flavor compound 2-acetyl-2-thiazoline. J. Agric. Food Chem. 1995, 43, 2946-2950.
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 2946-2950
    • Hofmann, T.1    Schieberle, P.2
  • 20
    • 0042073031 scopus 로고    scopus 로고
    • Studies on intermediates generating the flavour compounds 2-methyl-3-furanthiol, 2-acetyl-2-thiazoline, and Sotolon by Maillard-type reactions
    • Taylor, A. J., Mottram, D. S., Eds.; Royal Society of Chemistry: Cambridge, U.K.
    • Hofmann, T.; Schieberle, P. Studies on intermediates generating the flavour compounds 2-methyl-3-furanthiol, 2-acetyl-2-thiazoline, and Sotolon by Maillard-type reactions. In Flavour Science-Recent Developments; Taylor, A. J., Mottram, D. S., Eds.; Royal Society of Chemistry: Cambridge, U.K., 1996; pp 175-181.
    • (1996) Flavour Science-recent Developments , pp. 175-181
    • Hofmann, T.1    Schieberle, P.2
  • 21
    • 0001055803 scopus 로고    scopus 로고
    • Quantitative model studies on the effectivity of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol
    • Hofmann, T.; Schieberle, P. Quantitative model studies on the effectivity of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol. J. Agric. Food Chem. 1998a, 46, 235-241.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 235-241
    • Hofmann, T.1    Schieberle, P.2
  • 22
    • 0013607931 scopus 로고    scopus 로고
    • New and convenient syntheses of the important roasty, popcorn-like smelling food aroma compounds 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine from their corresponding cyclic α-amino acids
    • Hofmann, T.; Schieberle, P. New and convenient syntheses of the important roasty, popcorn-like smelling food aroma compounds 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine from their corresponding cyclic α-amino acids. J. Agric. Food Chem. 1998b, 46, 616-619.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 616-619
    • Hofmann, T.1    Schieberle, P.2
  • 23
    • 0005383967 scopus 로고
    • Autoxidation of Amadori compounds in the presence of copper ion and its effects on the oxidative damage to protein
    • Finot, P. A., Aeschbacher, H. U., Hurrell, R. F., Liardon, R., Eds.; Birkäuser Verlag: Basel
    • Kawakishi, S.; Uchida, K. Autoxidation of Amadori compounds in the presence of copper ion and its effects on the oxidative damage to protein. In Maillard Reaction in Food Processing, Human Nutritition and Physiology; Finot, P. A., Aeschbacher, H. U., Hurrell, R. F., Liardon, R., Eds.; Birkäuser Verlag: Basel, 1990; pp 475-480.
    • (1990) Maillard Reaction in Food Processing, Human Nutritition and Physiology , pp. 475-480
    • Kawakishi, S.1    Uchida, K.2
  • 24
    • 0001285566 scopus 로고
    • Non-enzymatic browning reactions of pentoses and amines
    • Ledl, F.; Severin, Th. Non-enzymatic browning reactions of pentoses and amines (in German). Z. Lebensm. Unters. Forsch. 1978, 167, 410-413.
    • (1978) Z. Lebensm. Unters. Forsch. , vol.167 , pp. 410-413
    • Ledl, F.1    Severin, Th.2
  • 25
    • 84954945905 scopus 로고
    • Quinoxalines derived from D-glucose and o-phenylenediamine in a weakly acidic medium
    • Monta, N.; Inoue, K., Takagi, M. Quinoxalines derived from D-glucose and o-phenylenediamine in a weakly acidic medium. Agric. Biol. Chem. 1981, 45, 2665-2668.
    • (1981) Agric. Biol. Chem. , vol.45 , pp. 2665-2668
    • Monta, N.1    Inoue, K.2    Takagi, M.3
  • 26
    • 84954922719 scopus 로고
    • Quinoxalines derived from disaccharides with o-phenylenediamine in a weakly acidic reflux conditions
    • Morita, N.; Inoue, K., Takagi, M. Quinoxalines derived from disaccharides with o-phenylenediamine in a weakly acidic reflux conditions. Agric. Biol. Chem. 1985, 49, 3279-3289.
    • (1985) Agric. Biol. Chem. , vol.49 , pp. 3279-3289
    • Morita, N.1    Inoue, K.2    Takagi, M.3
  • 27
    • 0002985341 scopus 로고
    • Formation of novel free radical products in an early stage of Maillard reaction
    • Namiki, M.; Hayashi, T. Formation of novel free radical products in an early stage of Maillard reaction. Prog. Food Nutr. Sci. 1981, 5, 81-91.
    • (1981) Prog. Food Nutr. Sci. , vol.5 , pp. 81-91
    • Namiki, M.1    Hayashi, T.2
  • 28
    • 0002458976 scopus 로고
    • A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation
    • Namiki, M.; Hayashi, T. A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation. ACS Symp. Ser. 1983, No. 215, 21-46.
    • (1983) ACS Symp. Ser. , vol.215 , pp. 21-46
    • Namiki, M.1    Hayashi, T.2
  • 29
    • 0000945315 scopus 로고
    • Detection of 5-hydroxymethyl-2-methyl-3(2H)-furanone and of α-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines
    • Nedvidek, W.; Ledl, F.; Fischer, P. Detection of 5-hydroxymethyl-2-methyl-3(2H)-furanone and of α-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines. Z. Lebensm. Unters. Forsch. 1992, 194, 222-228.
    • (1992) Z. Lebensm. Unters. Forsch. , vol.194 , pp. 222-228
    • Nedvidek, W.1    Ledl, F.2    Fischer, P.3
  • 30
    • 0000458908 scopus 로고    scopus 로고
    • Evaluation of the character impact odorants in fresh strawberry juice by quantitative measurements and sensory studies on model mixtures
    • Schieberle, P.; Hofmann, T. Evaluation of the character impact odorants in fresh strawberry juice by quantitative measurements and sensory studies on model mixtures. J. Agric. Food Chem. 1997, 45, 227-232.
    • (1997) J. Agric. Food Chem. , vol.45 , pp. 227-232
    • Schieberle, P.1    Hofmann, T.2
  • 31
    • 0001633337 scopus 로고
    • Structure of a colored Maillard reaction product formed from pentoses
    • Severin, Th.; Krönig, U. Structure of a colored Maillard reaction product formed from pentoses (in German). Chem. Microbiol. Technol. Lebensm. 1972, 1, 156-157.
    • (1972) Chem. Microbiol. Technol. Lebensm. , vol.1 , pp. 156-157
    • Severin, Th.1    Krönig, U.2
  • 32
    • 0010280614 scopus 로고    scopus 로고
    • Carbohydrate cleavage in the Maillard reaction
    • Taylor, A. J., Mottram, D. S., Eds.; Royal Society of Chemistry, Cambridge, U.K.
    • Weenen, H.; Apeldoorn, W. Carbohydrate cleavage in the Maillard reaction. In Flavour Science-Recent Developments; Taylor, A. J., Mottram, D. S., Eds.; Royal Society of Chemistry, Cambridge, U.K., 1996; pp 211-216.
    • (1996) Flavour Science-Recent Developments , pp. 211-216
    • Weenen, H.1    Apeldoorn, W.2
  • 33
    • 0023259759 scopus 로고
    • Glucose autoxidation and protein modification - The potential role of autoxidative glycosylation in diabetes
    • Wolff, S. P.; Dean, R. T. Glucose autoxidation and protein modification - the potential role of autoxidative glycosylation in diabetes. Biochem. J. 1987, 245, 243-250.
    • (1987) Biochem. J. , vol.245 , pp. 243-250
    • Wolff, S.P.1    Dean, R.T.2


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