Advertisement

Reaction Chemistry of Lactose: Non-Enzymatic Degradation Pathways and Their Significance in Dairy Products

  • J. O’Brien

Abstract

Milk products are especially sensitive to the effects of heat treatment encountered under conventional process and storage conditions because of an abundance of reactive functional groups: aldehyde group of lactose, ε-amino group of lysine and other reactive N-groups (e.g. indolyl group of tryptophan, imidazole group of histidine, guanidino group of arginine and the α-amino group of proteins and free amino acids).

Keywords

Food System Maillard Reaction Furfuryl Alcohol Maillard Reaction Product Amadori Product 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adachi, S. (1958) Formation of lactulose and tagatose from lactose in strongly heated milk. Nature, 181, 840–1.Google Scholar
  2. Adachi, S. and Patton, S. (1961) Presence and significance of lactulose in milk products: a review. J. Dairy Sci., 44, 1375–93.Google Scholar
  3. Alfawaz, M., Smith, J.S. and Jeon, I.J. (1994) Maillard reaction products as antioxidants in pre-cooked ground beef. Food Chem., 31, 311–18.Google Scholar
  4. Amaya, J., Lee, T-C. and Chichester, C.O. (1976) Biological inactivation of proteins by the Maillard reaction. Effect of mild heat on the tertiary structure of insulin. J. Agric. Food Chem., 24, 465–7.Google Scholar
  5. Anderson, T.R. and Quicke, G.V. (1984) An isotopic method for determining chemically reactive lysine based on succinylation. J. Sci. Food Agric., 35, 472–80.Google Scholar
  6. Andrews, G.R. (1984) Distinguishing pasteurized, UHT and sterilized milks by their lactulose content. J. Soc. Dairy Technol., 37, 92–6.Google Scholar
  7. Andrews, G.R. (1986) Formation and occurrence of lactulose in heated milk. J. Dairy Res., 53, 665–80.Google Scholar
  8. Andrews, G.R. (1989) Lactulose in heated milk, in Heat-Induced Changes in Milk, (P.F. Fox, ed.), Bulletin 238, International Dairy Federation, Brussels, pp. 45–52.Google Scholar
  9. Andrews, G.R. and Prasad, S.K. (1987) Effect of the protein, citrate and phosphate content of milk on formation of lactulose during heat treatment. J. Dairy Res., 54, 207-18.Google Scholar
  10. Angyal, S.J. (1984) The composition of reducing sugars in solution, Adv. Carbohydr. Chem. Biochem., 42, 15–68.Google Scholar
  11. Angyal, S.J. (1991) The composition of reducing sugars in solution: current aspects. Adv. Carbohydr. Chem. Biochem., 49, 19-35.Google Scholar
  12. Aoki, T., Matsumoto, T., Kako, Y., et al. (1994) Improvement of functional properties of ß-lactoglobulin by glucose-6-phosphate conjugation, in Maillard Reactions in Chemistry, Food and Health, T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien, and J.W. Baynes, (eds), Royal Society of Chemistry, Cambridge, p. 409.Google Scholar
  13. Armstrong, J.J., Hill, S.E. and Mitchell, J.R. (1994) Enhancement of the gelation of food macromolecules using the Maillard reaction and elevated temperatures, in Maillard Reactions in Chemistry, Food and Health, T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, (eds), Royal Society of Chemistry, Cambridge, pp. 159–63.Google Scholar
  14. Ashoor, S.H. and Zent, J.B. (1984) Maillard browning of common amino acids and sugars. J. Food Sci., 49, 1206–7.Google Scholar
  15. Assoumani, M.B., Nguyen, N.P., Lardinois, P.F., et al. (1990) Use of a lysine oxidase electrode for lysine determination in Maillard model reactions and in soybean meal hydrolysates. Lebensm. Wiss. Technol., 23, 322–7.Google Scholar
  16. Badoud, R., Hunston, F., Fay, L. and Pratz, G. (1990) Oxidative degradation of protein-bound Amadori products: formation of N-c-carboxymethyl lysine and N-carboxymethyl amino acids as indicators of the extent of non-enzymatic glycosylation, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds), Birkhäuser Verlag, Basel, pp. 79–84.Google Scholar
  17. Baisier, W.M. and Labuza, T.P. (1992) Maillard browning kinetics in a liquid model system. J. Agric. Food Chem., 40, 707–13.Google Scholar
  18. Beach, R.C. and Menzies, I.S. (1983) Lactulose and other non-absorbable sugars in infant milk foods. Lancet, I, 425–6.Google Scholar
  19. Beck, J., Ledl, F. and Severin, T. (1988) Formation of 1-deoxy-D-erythro-2,3hexodiulose from Amadori compounds. Carbohydr. Res., 177, 240–3.Google Scholar
  20. Bell, L.N. and Hageman, M.J. (1994) Differentiating between the effects of water activity and glass transition dependent mobility on a solid state chemical reaction: aspartame degradation. J. Agric. Food Chem., 42, 2398–401.Google Scholar
  21. Bell, L.N. and Labuza, T.P. (1992) pH of low-moisture solids. Trends Food Sci. Technol., 3, 271–4.Google Scholar
  22. Ben-Gera, I. and Zimmerman, G. (1972) Changes in the nitrogenous constituents of staple foods and feeds during storage. I. Decrease in the chemical availability of lysine. J. Food Sci. Technol., India,9, 113–18.Google Scholar
  23. Berg, H.E. (1993) Reactions of Lactose During Heat Treatment of Milk: A Quantitative Study, Ph.D. Thesis, Wageningen Agricultural University.Google Scholar
  24. Berg, H.E., van Boekel, M.A.J.S. and Jongen, W.M.F. (1990) Heating milk: a study of mutagenicity. J. Food Sci., 55, 1000–3, 1017.Google Scholar
  25. Berlin, E., Anderson, B.A. and Pallansch, M.J. (1973) Water sorption by dried dairy products stabilized with carboxymethyl cellulose. J. Dairy Sci., 56, 685–9.Google Scholar
  26. Bernhart, F.W., Gogliardi, E.D., Tomarelli, R.M. and Stribley, R.C. (1965)Google Scholar
  27. Lactulose in modified milk products for infant nutrition. J. Dairy Sci.,48,399–400.Google Scholar
  28. Bobbio, F.O., Bobbio, P.A. and Trevisan, L.M.V. (1973) Maillard reaction. II: catalytic effect of anions. Lebensm. Wiss. Technol., 6, 215–18.Google Scholar
  29. Buera, M.P. and Karel, M. (1993) Application of the WLF equation to describe the combined effects of moisture and temperature on non-enzymatic browning rates in food systems. J. Food Process. Preserv., 17, 31–45.Google Scholar
  30. Buera, M.P. and Karel, M. (1995) Effect of physical changes on the rates of non-enzymatic browning and related reactions. Food Chem., 52, 167–73.Google Scholar
  31. Buera, M.P., Chirife, J. and Resnik, S.L. (1990) Browning reactions of Heyns rearrangement products. Kinetics of the Maillard reaction during processing and storage. Nahrung, 34, 759–64.Google Scholar
  32. Burton, H. (1984) Review of the Progress of dairy science: the bacteriological, chemical, biochemical and physical changes that occur in milk at temperatures of 100–150°C. J. Dairy Res., 51, 341–63.Google Scholar
  33. Burvall, A., Asp, N-G., Bosson, A., José, C.S. and Dahlqvist, A. (1978) Storage of lactose-hydrolysed dried milk: effect of water activity on the protein nutritional value. J. Dairy Res., 45, 381–9.Google Scholar
  34. Buser, W. and Erbersdobler, H.F. (1985) Determination of furosine by gas-liquid chromatography. J. Chromatogr., 346, 363–8.Google Scholar
  35. Cabodevila, O., Hill, S.E., Armstrong, H.J., et al. (1994) Gelation enhancement of soy protein isolate using the Maillard reaction and high temperatures. J. Food Sci., 59, 872–5.Google Scholar
  36. Calvo, M.M. and de la Hoz, L. (1992) Flavour of heated milks. I. A review. Mt. Dairy J., 2, 69–81.Google Scholar
  37. Calvo, M.M. and Olano, A. (1989) Formation of galactose during heat treatment of milk and model systems. J. Dairy Res., 56, 737–40.Google Scholar
  38. Carpenter, K.J. (1960) The estimation of the available lysine in animal-protein foods. Biochem. J., 77, 604–10.Google Scholar
  39. Cerrutti, P., Resnik, S.L., Seldes, A. and Fontan, C.F. (1985) Kinetics of deteriorative reactions in model food systems of high water activity: glucose loss, 5-hydroxy-methylfurfural accumulation and fluorescence development due to nonenzymatic browning. J. Food Sci., 50, 627–30, 656.Google Scholar
  40. Chan, F. and Reineccius, G.A. (1994) The reaction kinetics for the formation of isovaleraldehyde, 2-acetyl-1-pyrroline, di(H)di(OH)-6-methylpyranone, phenylacetaldehyde, 5-methyl-2-phenyl-2-hexenal and 2-acetyl furan in model systems, in Maillard Reactions in Chemistry, Food and Health, (T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien, and J.W. Baynes, eds), Royal Society of Chemistry, Cambridge, pp. 131–9.Google Scholar
  41. Chiang, G.H. (1983) A simple and rapid high performance liquid chromatographic procedure for determination of furosine, lysine-reducing sugar derivative. J. Agric. Food Chem., 31, 1373–4.Google Scholar
  42. Chiang, G.H. (1988) High performance liquid chromatographic determination of c-pyrrole-lysine in processed food. J. Agric. Food Chem., 36, 506–9.Google Scholar
  43. Chung, S-Y., Swaisgood, H.E. and Catignani, G.L. (1986) Effects of alkali treatment and heat treatment in the presence of fructose on digestibility of food proteins as determined by an immobilized digestive enzyme assay (IDEA). J. Agric. Food Chem., 34, 579–84.Google Scholar
  44. Chuy, L.E. and Labuza, T.P. (1994) Caking and stickiness of dairy-based food powders as related to glass transition. J. Food Sci., 59, 43–6.Google Scholar
  45. Clamp, J.R., Hough, L., Hickson, J.L. and Whistler, R.L. (1961) Lactose. Adv. Carbohydr. Chem., 16, 159–206.Google Scholar
  46. Culver, C.A. and Swaisgood, H.E. (1989) Changes in the digestibility of dried casein and glucose mixtures occurring during storage at different temperatures and water activities. J. Dairy Sci., 72, 2916–20.Google Scholar
  47. De Bruyn, A., van Beeumen, J., Anteunis, M. and Verhegge, G. (1975) Proton NMR study of some D-aldohexapyranosyl-D-fructos(id)es in water-D2O. Bull. Soc. Chim. Belg. 84, 799–812.Google Scholar
  48. Desrosiers, T., Savoie, L., Bergeron, G. and Parent, G. (1989) Estimation of lysine damage in heated whey proteins by furosine determinations in conjunction with the digestion cell technique. J. Agric. Food Chem., 37, 1385–91.Google Scholar
  49. Dutra, R.C., Tarassuk, N.P. and Kleiber, M. (1958) Origin of the carbon dioxide produced in the browning reaction of evaporated milk. J. Dairy Sci., 41, 101–723.Google Scholar
  50. Dworschak, E. and Hegedus, M. (1974) Effect of heat treatment on the nutritive value of proteins in milk powder. Acta Aliment. Acad. Sci. Hung. 6, 337–47.Google Scholar
  51. Earley, R.A. and Hansen, A.P. (1982) Effect of process and temperature during storage on ultra-high temperature steam-injected milk. J. Dairy Sci., 65, 11–16.Google Scholar
  52. Eichner, K. and Ciner-Doruk, M. (1979) Formation and stability of Amadori compounds in low moisture model systems. Lebensm. Unters. Forsch., 168, 360–7.Google Scholar
  53. Eichner, K. and Ciner-Doruk, M. (1981) Early indicators of the Maillard reaction by analysis of reaction intermediates and volatile decomposition products. Prog, Food Nutr. Sci., 5, 115–35.Google Scholar
  54. Eichner, K. and Karel, M. (1972) The influence of water content and water activity on the sugar-amino browning reaction in model systems under various conditions. J. Agric. Food Chem., 20, 218–23.Google Scholar
  55. El-Shafei, M.M., Al-Amoudy, N.S. and Said, A.K. (1988) Effect of the drying process on the nutritive value of milk, Part 2. Biological evaluation. Nahrung, 32, 559–64.Google Scholar
  56. El Zeany, B-D. (1982) Oxidised lipids-proteins browning reaction. Part 7: effects of carbonyl group reactants. Riv. Ital. Sostanze Grasse, 59, 423–5.Google Scholar
  57. Erbersdobler, H.F. and Dehn-Müller, B. (1989) Formation of early Maillard products during UHT treatment of milk, in Heat-Induced Changes in Milk, (P.F. Fox, ed.), Bulletin 238, International Dairy Federation, Brussels, pp. 62–70.Google Scholar
  58. Erbersdobler, H.F., Dehn, B., Nangpal, A. and Reuter, H. (1987) Determination of furosine in heated milk as a measure of heat intensity during processing. J. Dairy Res., 54, 147–51.Google Scholar
  59. Evangelisti, F., Calcagno, C. and Zunin, P. (1993) Changes induced by Maillard reaction in milk formulas. Rivista Sci. Aliment. 22, 77–82.Google Scholar
  60. Evangelisti, F., Calcagno, C. and Zunin, P. (1994) Relationship between blocked lysine and carbohydrate composition of infant formulas. J. Food Sci., 59, 335–7.Google Scholar
  61. Feather, M.S. (1970) The conversion of D-xylose and D-glucuronic acid to 2-furaldehyde. Tetrahedron Lett., 48, 4141–5.Google Scholar
  62. Feather, M.S. (1981) Amine-assisted sugar dehydration reactions. Prog. Food Nutr. Sci., 5, 37–45.Google Scholar
  63. Feather, M.S. (1989) The formation of deoxylglycosuloses (deoxyosones) and their reactions during the processing of food, in Frontiers in Carbohydrate Research —1, R.P. Millane, J.N. Be Miller and R. Chandrasekaran, (eds.), Elsevier Science Publishers, New York, pp. 66–73.Google Scholar
  64. Ferretti, A. and Flanagan, V.P. (1971) The lactose-casein (Maillard) browning system: volatile components. J. Agric. Food Chem., 19, 245–9.Google Scholar
  65. Ferretti, A. and Flanagan, V.P. (1972) Steam volatile constituents of stale non-fat dry milk. The role of the Maillard reaction in staling. J. Agric. Food Chem., 20, 695–8.Google Scholar
  66. Finot, P.A., Deutsch, R. and Bujard, E. (1981) The extent of the Maillard reaction during the processing of milk. Prog. Food Nutr. Sci., 5, 345–5.Google Scholar
  67. Fox, P.F. (1981) Heat-induced changes in milk preceeding coagulation. J. Dairy Sci., 64, 2127–37.Google Scholar
  68. Franks, F. (1991) Water activity: a credible measure of food safety and quality? Trends Food Sci. Technol., 2, 68–72.Google Scholar
  69. Franzen, K., Singh, R.K. and Okos, M.R. (1990) Kinetics of non-enzymatic browning in dried skim milk. J. Food Eng., 11, 225–39.Google Scholar
  70. Friedman, M. and Molnar-Perl, I. (1990) Inhibition of browning by sulphur amino acids. I. Heated amino acid-glucose systems. J. Agric. Food Chem., 38, 1642–7.Google Scholar
  71. Furniss, D.E., Vuichoud, J., Finot, P.A. and Hurrell, R.F. (1989) The effect of Maillard reaction products on zinc metabolism in the rat. Br. J. Nutr., 62, 63–949.Google Scholar
  72. Geier, H. (1984) Untersuchungen zur analytischen kontrolle der warmebelastung von konsummilch, PhD Thesis, Technische Universität, Munich.Google Scholar
  73. Geier, H. and Klostermeyer, H. (1980) Enzymatic determination of lactulose. Z. Lebensm. Unters. Forsch., 171, 443–5.Google Scholar
  74. Geier, H. and Klostermeyer, H. (1983) Formation of lactulose during heat treatment of milk. Milchwissenschaft, 38, 475–7.Google Scholar
  75. Ghiron, A.F., Quack, B., Mawhinney, T.P. and Feather, M.S. (1988) Studies on the role of 3-deoxy-D-erythro-glucosulose (3-deoxyglucosone) in non-enzymatic browning. Evidence for involvement in a Strecker degradation. J. Agric. Food Chem., 36, 677–80.Google Scholar
  76. Glomb, M., Lederer, M. and Ledl, F. (1991) 5-Hydroxymethyl-3-(2H)-furanone, 5-(1,2-dihydroxyethyl)-3(2H)-furanone and 5-hydroxy-2H-pyran-3(6H)-one: reactive intermediates in the Maillard reaction of hexoses and pentoses. Z. Lebensm. Unters. Forsch., 193, 237–41.Google Scholar
  77. Gopalan, S., Gracy, A.T. and Srinivasan, A. (1994) Deamination of basic amino acids in protein using active carbonyl compounds produced by the Maillard reaction, in Maillard Reactions in Chemistry, Food and Health, (T.P. Labuza, G.A. Reineccius, V.M. Monnier, J.M. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, p. 412.Google Scholar
  78. Gothwal, P.P. and Bhavadasan, M.K. (1991) Proteolytic hydrolysis of milk proteins as influenced by browning. Indian J. Dairy Sci., 44, 501–9.Google Scholar
  79. Gothwal, P.P. and Bhavadasan, M.K. (1992) Influence of levels of total soluble salt, citrate and phosphate on browning in milk. J. Dairying Foods Home Sci., 11, 95–102.Google Scholar
  80. Greig, B.D. and Payne, G.A. (1985) Epimerization of lactose to free lactulose in heated model milk systems. J. Dairy Res., 52, 409–17.Google Scholar
  81. Griffith, R. and Hammond, E.G. (1989) Generation of Swiss cheese flavour components by the reaction of amino acids with carbonyl compounds. J. Dairy Sci., 72, 604–13.Google Scholar
  82. Hall, G. and Andersson, J. (1985) Flavour changes in whole milk powder during storage. III. Relationships between flavour properties and volatile compounds. J. Food Qual., 7, 237–53.Google Scholar
  83. Hartkopf, J. and Erbersdobler, H.F. (1993) Stability of furosine during ion-exchange chromatography in comparison with reversed-phase high-performance liquid chromatography. J. Chromatogr., 635, 151–4.Google Scholar
  84. Hartkopf, J. and Erbersdobler, H.F. (1994) Model experiments on the formation of N-c-carboxymethyl lysine in food products. Z. Lebensm. Unters. Forsch., 198, 15–19.Google Scholar
  85. Hayase, F. and Kato, H. (1986) Low-molecular Maillard reaction products and their formation mechanisms, in Amino-Carbonyl Reactions in Food and Biological Systems, ( M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 39–48.Google Scholar
  86. Hayashi, T. and Namiki, M. (1981) On the mechanism of free radical formation during browning reaction of sugars and amino compounds, Agric. Biol. Chem., 45, 933–9.Google Scholar
  87. Hayashi, T. and Namiki, M. (1986) Role of sugar fragmentation in the Maillard reaction, in Amino-Carbonyl Reactions in Food and Biological Systems, ( M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 29–38.Google Scholar
  88. Hayashi, T., Hoshii, Y. and Namiki, M. (1983) On the yellow product and browning of the reaction of dehydroascorbic acid with amino acids. Agric. Biol. Chem., 47, 1003–9.Google Scholar
  89. Hendrickse, R.G., Wooldridge, M.A.W. and Russell, A. (1977) Lactulose in baby milks causing diarrhoea simulating lactose intolerance. Br. Med. J., I, 1194–5.Google Scholar
  90. Henle, R., Walter, H. and Klostermeyer, H. (1991) Evaluation of the extent of the early Maillard reaction in milk products by direct measurement of the Amadori product lactuloselysine. Z. Lebensm. Unters. Forsh., 193, 119–22.Google Scholar
  91. Henle, T., Walter, A.W. and Klostermeyer, H. (1994) Simultaneous determination of protein-bound Maillard products by ion exchange chromatography and photodiode array detection, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 195–200.Google Scholar
  92. Heusinger, H. (1986) Formation and polymerisation of malonaldehyde during irradiation of aqueous solutions of 1-glucose and lactose with ultrasound. Carbohydr. Res., 154, 37–48.Google Scholar
  93. Hidalgo, F.J. and Zamora, R. (1993) Non-enzymatic browning and fluorescence development in (E)-4, 5-epoxy-(E)-2-heptenal/lysine model system. J. Food Sci., 58, 667–70.Google Scholar
  94. Hodge, J.E. (1967) Origin of flavor in foods. Non-enzymatic browning reactions, in Chemistry and Physiology of Flavours, ( H.W. Schultz, E.A. Day and L.M. Libbey, eds.), AVI Publishing, Westport, CT, pp. 465–90.Google Scholar
  95. Horak, F.P. and Kessler, H.G. (1981) The influence of UHT heating and sterilization on lysine in milk. Milchwissenschaft, 36, 543–7.Google Scholar
  96. Huh, K.T., Toba, T. and Adachi, S. (1991) Oligosaccharide structures formed during acid hydrolysis of lactose. Food Chem., 39, 39–49.Google Scholar
  97. Hurrell, R.F. (1990) Influence of the Maillard reaction on the nutritive value of foods, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 245–57.Google Scholar
  98. Hurrell, R.F. and Carpenter, K.J. (1974) Mechanisms of heat damage in proteins. 4. The reactive lysine content of heat-damaged material as measured in different ways. Br. J. Nutr., 32, 589–604.Google Scholar
  99. Hurrell, R.F. and Carpenter, K.J. (1975) The use of three dye-binding procedures for the assessment of heat damage to food proteins. Br. J. Nutr., 33, 101–15.Google Scholar
  100. Hurrell, R.F., Lerman, P. and Carpenter, K.J. (1979) Reactive lysine in foodstuffs as measured by a rapid dye-binding procedure. J. Food Sci., 44, 1221–7, 12–31.Google Scholar
  101. Huss, V.W. (1974a) Temporal development of lysine damage during storage of dried skim-milk under various conditions. Landwirtsch. Forsch., 27, 199–210.Google Scholar
  102. Huss, V.W. (1974b) Amino acid damage during processing and storage of whey and whey powder. Z. Tier Physiol., Tiernahr., Futtermittelkde, 34, 60–7.Google Scholar
  103. IDF (1991) Heat-Treated Milk — Determination of Lactulose Content, High Performance Liquid Chromatography (Reference Method). Standard 147, International Dairy Federation, Brussels.Google Scholar
  104. Igaki, N., Sakai, M., Hata, F., et al. (1990) The role of 3-deoxyglucosone in the Maillard reaction, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 103–8.Google Scholar
  105. Isaacs, N.S. (1987) Physical Organic Chemistry, Longman Scientific and Technical, London, pp. 386–400.Google Scholar
  106. Izzo, H.V. and Ho, C-T. (1992) Peptide-specific Maillard reaction products: a new pathway for flavor chemistry. Trends Food Sci. Technol., 3, 253–7.Google Scholar
  107. Jaddou, H.A., Pavey, J.A. and Manning, D.J. (1978) Chemical analysis of flavour volatiles in heat-treated milks. J. Dairy Res., 45, 391–403.Google Scholar
  108. Jagerstad, M., Laser Reuterswärd, A., Oste, R., et al. (1983) Creatinine and Maillard reaction products as precursors of mutagenic compounds formed in fried beef, in The Maillard Reaction in Foods and Nutrition, ( G.R. Waller and M.S. Feather, eds.), American Chemical Society, Washington, DC, pp. 507–19.Google Scholar
  109. Jimenez-Perez, S., Corzo, N., Morales, F.J., et al. (1992) Effect of storage temperature on lactulose and 5-hydroxymethyl-furfural formation in UHT milk. J. Food Prot., 55, 30–46.Google Scholar
  110. Kaanane, A. and Labuza, T.P. (1989) The Maillard reaction in foods, in The Maillard Reaction in Aging, Diabetes and Nutrition, ( J.W. Baynes and V.M. Monnier, eds.), Alan R. Liss Inc., New York, pp. 301–27.Google Scholar
  111. Kakade, M.L. and Liener, I.E. (1969) Determination of available lysine in proteins. Anal. Biochem., 27, 273–80.Google Scholar
  112. Kaneko, S., Okitani, A., Hayase, F. and Kato, H. (1991) Identification of an intermediate product and formation mechanisms of cross-linking compounds from N-a-acetyltryptophan and hexanal. Agric. Biol. Chem., 55, 723–30.Google Scholar
  113. Karel, M. and Buera, M.P. (1994) Glass transition and its potential effects on kinetics of condensation reactions and in particular on non-enzymatic browning, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 164–9.Google Scholar
  114. Karel, M. and Saguy, I. (1991) Effects of water on diffusion in food systems, in Water Relationships in Foods, ( H. Levine and L. Slade, eds.), Plenum Press, New York, pp. 157–73.Google Scholar
  115. Karmas, R, and Karel, M. (1994) The effect of glass transition on Maillard browning in food models, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 182–7.Google Scholar
  116. Karmas, R., Buera, M.P. and Karel, M. (1992) Effect of glass transition on rates of nonenzymatic browning in food systems. J. Agric. Food Chem., 40, 873–9.Google Scholar
  117. Kato, R. (1986) Metabolic activation of mutagenic heterocyclic aromatic amines from protein pyrolysates. Crit. Rev. Toxicol., 16, 307–48.Google Scholar
  118. Kato, H., Matsumura, M. and Hayase, F. (1981a) Chemical changes in casein heated with and without D-glucose in the powdered state or in an aqueous solution. Food Chem., 7, 159–68.Google Scholar
  119. Kato, Y., Watanabe, K. and Sato, Y. (1981b) Effect of some metals on the Maillard reaction of ovalbumin. J. Agric. Food Chem., 29, 540–3.Google Scholar
  120. Kato, Y., Watanabe, K. and Sato, Y. (1981c) Effect of Maillard reaction on some physical properties of ovalbumin. J. Food Sci., 46, 1835–9.Google Scholar
  121. Kato, Y., Watanabe, K. and Sato, Y. (1983) Conformational stability of ovalbumin reacted with glucose in a Maillard reaction. Agric. Biol. Chem., 47, 1925–6.Google Scholar
  122. Kato, Y., Matsuda, T., Kato, N., et al. (1986) Browning and insolubilization of ovalbumin by the Maillard reaction with some aldohexoses. J. Agric. Food Chem., 34, 351–5.Google Scholar
  123. Kato, Y., Matsuda, T., Kato, N. and Nakamura, R. (1988) Browning and protein polymerization induced by amino-carbonyl reaction of ovalbumin with glucose and lactose. J. Agric. Food Chem., 36, 806–9.Google Scholar
  124. Kato, Y., Matsuda, T., Kato, N. and Nakamura, R. (1989) Maillard reaction of disaccharides with protein: suppressive effect of non-reducing and pyranoside groups on browning and protein polymerization. J. Agric. Food Chem., 37, 1077–81.Google Scholar
  125. Kato, Y., Matsuda, T., Kato, N. and Nakamura, R. (1990) Maillard reaction in sugar-protein systems, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 97–102.Google Scholar
  126. Kato, Y., Matsuda, T., Kato, N. and Nakamura, R. (1994) Analysis of lactose-protein Maillard complexes in commercial milk products by using specific monoclonal antibodies, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 188–94.Google Scholar
  127. Keeney, M. and Bassette, R. (1959) Detection of intermediate compounds in the early stages of browning reaction in milk products. J. Dairy Sci., 42, 945–60.Google Scholar
  128. King-Morris, M.J. and Serianni, A.S. (1986) Hydroxide-catalyzed isomerization of D-[l-13C] mannose: evidence for the involvement of 3,4-enediols. Carbohydr. Res., 154, 29–36.Google Scholar
  129. Kinsella, J.E., Whitehead, D.M., Brady, J. and Bringe, N.A. (1989) Milk proteins: possible relationships of structure and function, in Developments in Dairy Chemistry — 4. Functional Milk Proteins, ( P.F. Fox, ed.), Elsevier Applied Science, London, pp. 55–95.Google Scholar
  130. Klostermeyer, H. and Geier, H. (1983) Heat treatment of milk: characterization and control. Dtsche. Milchwirtsch., 34, 1667–73.Google Scholar
  131. Kowalewska, J., Zelazowska, H., Babuchowski, A., et al. (1985) Isolation of aroma-bearing material from Lactobacillus helveticus culture and cheese. J. Dairy Sci., 68, 2165–71.Google Scholar
  132. Kumar, V. and Banker, G.S. (1994) Maillard reaction and drug stability, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 164–9.Google Scholar
  133. Labuza, T.P. (1980) The effect of water activity on reaction kinetics of food deterioration. Food Technol., 34, 36–41.Google Scholar
  134. Labuza, T.P. (1994) Interpreting the complexity of the kinetics of the Maillard reaction, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 176–81.Google Scholar
  135. Labuza, T.P. and Massaro, S.A. (1990) Browning and amino acid loss in model total parenteral nutrition solutions. J. Food Sci., 55, 821–6.Google Scholar
  136. Labuza, T.P. and Saltmarch, M. (1981) Kinetics of browning and protein quality loss in whey powders during steady state and non steady state storage conditions. J. Food Sci., 47, 92–6, 113.Google Scholar
  137. Labuza, T.P., Tannenbaum, S.R. and Karel, M. (1970) Water content and stability of low-moisture and intermediate moisture foods. Food Technol., 24, 543–50.Google Scholar
  138. Lea, C.H. (1948) The reaction between milk protein and reducing sugar in the `dry’ state. J. Dairy Res., 15, 369–76.Google Scholar
  139. Lea, C.H. and Hannan, R.S. (1949) Studies of the reaction between proteins and reducing sugars in the “dry” state. I. The effect of water, of pH and of temperature on the primary reaction between casein and glucose. Biochim. Biophys. Acta, 3, 313–25.Google Scholar
  140. Leahy, M.M. and Warthesen, J.J. (1983) The influence of Maillard browning and other factors on the stability of free tryptophan. J. Food Process. Preserv., 7, 25–39.Google Scholar
  141. Ledl, F. and Schleicher, E. (1990) New aspects of the Maillard reaction in foods and in the human body. Angew Chem Int Ed Engl., 29, 565–94.Google Scholar
  142. Ledl, F., Fritsch, G., Hiebl, J., et al. (1986) Degradation of Maillard products, in Amino-Carbonyl Reactions in Food and Biological Systems, (M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 17382.Google Scholar
  143. Lee, H.S. and Nagy, S. (1990) Relative reactivities of sugars in the formation of 5hydroxymethylfurfural in sugar-catalyst model systems. J. Food Process. Preserv., 14, 171–8.Google Scholar
  144. Lindemann-Schneider, U. and Fennema, O. (1989) Stability of lysine, methionine and tryptophan in dried whey concentrate during storage. J. Dairy Sci., 72, 1740–7.Google Scholar
  145. Loncin, M., Bimbenet, J.J. and Lenges, J. (1968) Influence of the activity of water on the spoilage of foodstuffs. J. Food Technol., 3, 131–42.Google Scholar
  146. Longenecker, J.B. and Hause, N.L. (1959) Relationships between plasma amino acids and composition of the ingested protein. Arch. Biochem. Biophys., 84, 46–59.Google Scholar
  147. Löscher, J., Kroh, L., Westphal, G. and Vogel, J. (1991) L–Ascorbic acid — a carbonyl component of non–enzymatic browning reactions, 2 Amino–carbonyl reactions of L–ascorbic acid. Z. Lebensm, Unters. Forsch., 192, 32–3–7.Google Scholar
  148. Lüdemann, G. and Erbersdobler, H.F. (1990) Model experiments on the formation of N-c-carboxymethyllysine (CML) in foods, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, (P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhaüser Verlag, Basel, pp. 91–6.Google Scholar
  149. Martinez-Castro, I., Olano, A.and Corzo, N. (1986) Modifications and interactions of lactose with mineral components of milk during heating processes. Food Chem., 21, 211–21.Google Scholar
  150. Matsuda, T., Kato, Y., Watanabe, K. and Nakamura, R. (1985a) Direct evaluation of 13-lactoglobulin in early Maillard reaction using an antibody specific to protein-bound lactose. J. Agric. Food Chem., 33, 1193–6.Google Scholar
  151. Matsuda, T., Kato, Y., Watanabe, K. and Nakamura, R. (1985b) Immunochemical properties of proteins glycosylated through Maillard reaction: ß-lactoglobulin-lactose and ovalbumin-glucose systems. J. Food Sci., 50, 618–21.Google Scholar
  152. Matsuda, T., Kato, Y., Watanabe, K. and Nakamura, R. (1986) Immunochemical analysis of protein lactosylation using antibody specific to e-deoxylactulosyl lysine, in Amino-Carbonyl Reactions in Food and Biological Systems, ( M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 411–19.Google Scholar
  153. Matsuda, T., Ishiguro, H., Okubo, I., et al. (1990) Immunodominancy and antigenic structure of lactose-protein Maillard adduct, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, (P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 297302.Google Scholar
  154. Matsuda, T., Kato, Y. and Nakamura, R. (1991) Lysine loss and polymerization of bovine 0–lactoglobulin by amino carbonyl reaction with lactulose (4–0–13–Dgalactopyranosyl–D–fructose). J. Agric. Food Chem., 39, 1201 – 4.Google Scholar
  155. Mauron, J. (1981) The Maillard reaction in food: a critical review from the nutritional stand point. Prog. Food Nutr. Sci., 5, 5–35.Google Scholar
  156. Mauron, J. and Bujard, E. (1964) Guanidation, an alternative approach to the determination of available lysine in foods, in Proc. 6th Int. Congr. Nutrition, ( C.F. Mills and R. Passmore, eds.), E. and S. Livingstone Ltd., London, p. 489.Google Scholar
  157. McGookin, B.J. (1991) Casein-sugar reaction products as antioxidants. Food Res. Q., 51, 55–9.Google Scholar
  158. Mijares, R.M., Park, G.L., Nelson, D.B. and McIver, R.C. (1986) HPLC analysis of HMF in orange juice. J. Food Sci., 55, 843–4.Google Scholar
  159. Miller, R.E. and Cantor, S.M. (1952) 2-Hydroxyacetylfuran from sugars. J. Am. Chem. Soc., 74, 5236–7.Google Scholar
  160. Min, D.B. and Lee, S-H. (1990) Gas chromatographic determination of carbon dioxide in non-fat dry milk during non-enzymic browning reaction. J. Sci. Food Agric., 53, 93–9.Google Scholar
  161. Minifie, B. (1979) A review of the processes for the manufacture of milk chocolate. Manuf. Confect., 59 (10), 43–8.Google Scholar
  162. Mizota, T., Tamura, Y., Tornita, M. and Okonogi, S. (1987) Lactulose as a sugar with physiological significance, Bulletin 212, International Dairy Federation, Brussels, pp. 69–76.Google Scholar
  163. Moll, N. and Gross, B. (1981) Isolation and purification of Amadori compounds by semi-preparative reversed-phase high performance liquid chromatography. J. Chromatogr., 206, 186–92.Google Scholar
  164. Moller, A.B. (1981) Chemical changes in ultra heat treated milk during storage. Prog. Food Nutr. Sci., 5, 357–68.Google Scholar
  165. Moller, A.B., Andrews, A.T. and Cheeseman, G.C. (1977a) Chemical changes in ultra-heat-treated milk during storage. I. Hydrolysis of casein by incubation with pronase and a peptidase mixture. J. Dairy Res., 44, 259–66.Google Scholar
  166. Moller, A.B., Andrews, A.T. and Cheeseman, G.C. (1977b) Chemical changes in ultra-heat-treated milk during storage. II. Lactuloselysine and fructoselysine formation by the Maillard reaction. J. Dairy Res., 44, 267–75.Google Scholar
  167. Molner-Perl, I. and Friedman, M. (1990) Inhibition of browning by sulfur amino acids. 2. Fruit juices and protein-containing foods. J. Agric. Food Chem., 38, 1648–51.Google Scholar
  168. Montgomery, E.M. and Hudson, C.S. (1930) Relations between rotatory power and structure in the sugar group. XXVII. Synthesis of a new disaccharide ketose (lactulose) from lactose. J. Am. Chem. Soc., 52, 2101–6.Google Scholar
  169. Mottu, F. and Mauron, J. (1967) The differential determination of lysine in heated milk. II. Comparison of the in vitro methods with the biological evaluation. J. Sci. Food Agric., 18, 57–62.Google Scholar
  170. Nakamura, S., Kato, A. and Kobayashi, K. (1992) Enhanced antioxidative effect of ovalbumin due to covalent binding of polysaccharides. J. Agric. Food Chem., 40, 2033–7.Google Scholar
  171. Nakamura, S., Kobayashi, K. and Kato, A. (1994) Role of positive charge of lysozyme in the excellent emulsifying properties of Maillard-type lysozyme-polysaccharide conjugate. J. Agric. Food Chem., 42, 2688–91.Google Scholar
  172. Namiki, M. and Hayashi, T. (1983) A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation, in The Maillard Reaction in Foods and Nutrition, ( G.R. Waller and M.S. Feather, eds.), American Chemical Society, Washington, DC, pp. 21–46.Google Scholar
  173. Namiki, M., Terao, A., Ueda, S. and Hayashi, T. (1986) Deamination of lysine in protein by reaction with oxidized ascorbic acid or active carbonyl compound produced by Maillard reaction, in Amino-Carbonyl Reactions in Food and Biological Systems, ( M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 105–14.Google Scholar
  174. Nangpal, A. and Reuter, H. (1987) Formation of lactulose during UHT-treatment of whole milk. Milschwissenschaft, 42, 298–301.Google Scholar
  175. Nielsen, H.K., Löliger, J. and Hurrell, R.F. (1985a) Reactions of proteins with oxidizing lipids. 1. Analytical measurements of lipid oxidation and of amino acid losses in a whey protein-methyl linolenate model system. Br. J. Nutr., 53, 61–73.Google Scholar
  176. Nielsen, H.K., De Weck, D., Finot, P.A. et al. (1985b) Stability of tryptophan during food processing and storage. 1. Comparative losses of tryptophan, lysine and methionine in different model systems. Br. J. Nutr., 53, 281–92.Google Scholar
  177. Nielsen, H.K., Klein, A. and Hurrell, R.F. (1985c) Stability of tryptophan during food processing and storage. 2. A comparison of methods used for the measurement of tryptophan losses in processed foods. Br. J. Nutr., 53, 293–300.Google Scholar
  178. Nursten, H.E. (1990) Key mechanistic problems posed by the Maillard reaction, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 145–53.Google Scholar
  179. Obretanov, T.D., Argirov, O.K. and Rashkov, I.B. (1983) On melanoidin formation with furfural participation: synthesis of melanoidins from furfural and glycine. J. Food Process. Preserv., 7, 105–13.Google Scholar
  180. O’Brien, J. (1988) Nutritional and Toxicological Aspects of the Maillard Browning Reaction, PhD Thesis, National University of Ireland, Cork.Google Scholar
  181. O’Brien, J. (1995a) Heat induced changes in lactose:- isomerization, degradation, Maillard browning, in Heat-Induced Changes in Milk, (P.F. Fox, ed.), Special Issue 9501, International Dairy Federation, Brussels, pp. 134–70.Google Scholar
  182. O’Brien J. (1995b) Nutritional value of milk protein hydrolysates. J. Nutr., 125, 1956.Google Scholar
  183. O’Brien, J. and Morrissey, P.A. (1989a) The Maillard reaction in milk products, in Heat-Induced Changes in Milk, (P.F. Fox, ed.), Bulletin 238, International Dairy Federation, Brussels, pp. 53–61.Google Scholar
  184. O’Brien, J. and Morrissey, P.A. (1989b) Nutritional and toxicological aspects of the Maillard browning reaction in foods. Crit. Rev. Food Sei Nutr., 28, 211–48.Google Scholar
  185. Okitani, A., Kaneko, S., Tashiro, Y., et al. (1986) Polymerization of proteins and impairment of their amino acid residues due to vaporized hexanal, in Amino-Carbonyl Reactions in Food and Biological Systems, ( M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 125–34.Google Scholar
  186. Olano, A. and Calvo, M.M. (1989) Kinetics of lactulose, galactose and epilactose formation during heat-treatment of milk. Food Chem., 34, 239–48.Google Scholar
  187. Olano, A. and Martinez-Castro, I. (1981) Formation of lactulose and epilactose from lactose in basic media. A quantitative study. Milchwissenschaft, 36, 533–36.Google Scholar
  188. Olano, A., Calvo, M.M. and Corzo, N. (1989) Changes in the carbohydrate fraction of milk during heating processes. Food Chem., 31, 259–65.Google Scholar
  189. Oste, R.E., Brandon, D.L., Bates, A. and Friedman, M. (1990) Antibody-binding to a Maillard reacted protein, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 303–8.Google Scholar
  190. Pagliarini, E., Vernile, M. and Peri, C. (1990) Kinetic study on color changes in milk due to heat. J. Food Sci., 55, 1766–7.Google Scholar
  191. Palombo, R., Gertler, A. and Saguy, I. (1984) A simplified method for determination of browning in dairy powders. J. Food Sci., 49, 1609–13.Google Scholar
  192. Pappas, C.P. and Rothwell, J. (1991) The effect of heating, alone or in the presence of calcium or lactose, on calcium binding to milk proteins. Food Chem., 42, 183–201.Google Scholar
  193. Park, Y-H. and Hong, Y-H. (1991) Changes in undenatured whey protein and available lysine contents in heat treated market milks. J. Korean Soc. Food Nutr., 20, 546–50.Google Scholar
  194. Patton, S. (1950a) Studies of heated milk. I. Formation of 5-hydroxymethyl-2furfural. J. Dairy Sci., 34, 324–8.Google Scholar
  195. Patton, S. (1950b) Studies of heated milk. III. Mode of formation of certain furan compounds. J. Dairy Sci., 33, 904–10.Google Scholar
  196. Patton, S. (1955) Browning and associated changes in milk and its products. J. Dairy Sci., 38, 457–78.Google Scholar
  197. Pavlovic, S., Santos, R.C. and Glória, M.B.A. (1994) Maillard reaction during the processing of `doce de leite’. J. Sci. Food Agric., 66, 129–32.Google Scholar
  198. Perlin, A.S., Herve du Penhoat, P. and Isbell, H.S. (1973) Carbon 13 and hydroxyl proton NMR spectra of ketoses. A conformational and compositional description of keto-hexoses in solution, in Carbohydrates in Solution, American Chemical Society, Washington, DC, pp. 39–50.Google Scholar
  199. Peterson, B.I., Tong, C-H., Ho, C-T. and Welt, B.A. (1994) Effect of moisture content on Maillard browning kinetics of a model system during microwave heating. J. Agric.Food Chem., 42, 1884–7.Google Scholar
  200. Petriella, C., Resnik, S.L., Lozano, R.D. and Chirife, J. (1985) Kinetics of deteriorative reactions in model food systems of high water activity: color changes due to non-enzymatic browning. J. Food Sci., 50, 622–6.Google Scholar
  201. Petriella, C., Chirife, J., Resnik, S.L. and Lozano, R.D. (1988) Correlation between induction time and rate of browning in heated model solutions of glucose and lysine, Int. J. Food Sci. Technol., 23, 415–18.Google Scholar
  202. Pham, C.B. and Cheftel, J.C. (1990) Influence of salts, amino acids and urea on the non-enzymatic browning of the protein-sugar system. Food Chem., 37, 251–60.Google Scholar
  203. Piergiovanni, L., De Noni, I., Fava, P. and Schiraldi, A. (1989) Nonenzymatic browning in processed cheeses. Ital. J. Food Sci., 1, 11–20.Google Scholar
  204. Piklova, L., Pokorny, J. and Davidek, J. (1990) Browning reactions of Heyns rearrangement products. Kinetics of the Maillard reaction during processing and storage. Nahrung, 34, 759–64.Google Scholar
  205. Pischetsrieder, M. and Severin. T. (1994) The Maillard reaction of disaccharides, in Maillard Reactions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 37–42.Google Scholar
  206. Pokorny, J., Pilova, L., Davidek, J. and Valentova, H. (1988) Effect of Amadori rearrangement products on the non-enzymatic browning in model systems. Nahrung, 32, 767–776.Google Scholar
  207. Porretta, S. and Sandei, L. (1991) Determination of 5-(hydroxymethyl) -2 furfural (HMF) in tomato products: proposal of a rapid HPLC method and its comparison with the colorimetric method. Food Chem., 39, 51–7.Google Scholar
  208. Potman, R.P. and van Wijk, T.A. (1989) Mechanistic studies of the Maillard reaction with emphasis on phosphate-mediated catalysis, in Thermal Generation of Aromas, (T.M. Parliment, R.J. McGorrin and C-T. Ho, eds.), American Chemical Society, Washington, DC, pp. 182–95.Google Scholar
  209. Powell, R.C.T. and Spark, A.A. (1971) Effect of zirconium and aluminium compounds and pH on the Maillard reaction. J. Sci. Food Agric., 22, 596–9.Google Scholar
  210. Rabasseda, J., Rauret, G. and Galceran, M.T. (1988) Liquid chromatographic determination of available lysine in soybean and fish meal. J. Assoc. Off. Anal. Chem., 71, 350–7.Google Scholar
  211. Ramshaw, E.H. and Dunstone, E.A. (1969) Volatile compounds associated with the off-flavour in stored casein. J. Dairy Res., 36, 215–23.Google Scholar
  212. Resmini, P., Pellegrino, L. and Battelli, G. (1990) Accurate quantification of furosine in milk and dairy products by a direct HPLC method. Ital. J. Food Sci., 3, 173–83.Google Scholar
  213. Rendleman, J.A. and Inglett, G.E. (1990) The influence of Cue+ in the Maillard reaction. Carbohydrate Res., 201, 311–26.Google Scholar
  214. Reutter, M. and Eichner, K. (1989) Separation and determination of Amadori compounds by high pressure liquid chromatography and post column reaction. Z. Lebensm. Unters. Forsch., 188, 28–35.Google Scholar
  215. Rogers, A. and Shibamoto, T. (1982) Mutagenicity of the products obtained from heated milk systems. Food Chem. Toxicol., 20, 259–63.Google Scholar
  216. Roos, Y. and Karel, M. (1992) Crystallization of amorphous lactose. J. Food Sci., 57, 775–7.Google Scholar
  217. Rowan, A.M., Moughan, P.J. and Wilson, M.N. (1992) Effect of hydrolysis time on the determination of the amino acid composition of diet, ileal digesta and feces samples and on the determination of dietary amino acid digestibility coefficients. J. Agric. Food Chem., 40, 981–5.Google Scholar
  218. Saltmarch, M., Vagnini-Ferrari, M. and Labuza, T.P. (1981) Theoretical basis and application of kinetics to browning in spray-dried whey food systems. Prog. Food Nutr. Sci., 5, 331–44.Google Scholar
  219. Scanlan, R.A., Lindsay, R.C., Libbey, L.M. and Day, E.A. (1968) Heat-induced volatile compounds in milk. J. Dairy Sci., 51, 1001–7.Google Scholar
  220. Schirle-Keller, J.P. and Reineccius, G.A. (1992) Reaction kinetics for the formation of oxygen-containing heterocyclic compounds in model systems, in Flavour Precursors. Thermal and Enzymatic Conversions, (R. Teranishi, G.R. Takeoka, M. Guntert, eds.), American Chemical Society, Washington, DC, pp. 244–58.Google Scholar
  221. Sekizawa, J. and Shibamoto, T. (1986) Salmonella/microsome mutagenicity tests of heat-processed milk samples. Food Chem. Toxicol., 24, 987–8.Google Scholar
  222. Shallenberger, R.S. (1984) Nature of the amino acid catalysis of the glucose mutarotation reaction. Food Chem., 15, 1–7.Google Scholar
  223. Sheldon, S.A., Russell, G.F. and Shibamoto, T. (1986) Photochemical and thermal activation of model Maillard reaction systems, in Amino-Carbonyl Reactions in Food and Biological Systems(M. Fujimaki, M. Namiki and H. Kato, eds.), Elsevier Science Publishers, Amsterdam, pp. 145–54.Google Scholar
  224. Sherr, B., Lee, C.M. and Jelesciewicz, C. (1989) Absorption and metabolism of lysine Maillard products in relation to utilization of L-lysine. J. Agric. Food Chem., 37, 119–22.Google Scholar
  225. Shibamoto, T. and Yeo, H. (1992) Flavour compounds formed from lipids by heat treatment, in Flavour Precursors. Thermal and Enzymatic Conversions, (R. Teranishi, G.R. Takeoka and M. Güntert, eds.), American Chemical Society, Washington, DC, pp. 175–82.Google Scholar
  226. Shipe, W.F., Bassette, R., Deane, D.D., et al. (1978) Off-flavours of milk: nomenclature, standards and bibliography. J. Dairy Sci., 61, 855–69.Google Scholar
  227. Shiratsuchi, H., Shimoda, M., Imayoshi, K., et al. (1994) Volatile flavour compounds in spray-dried skim milk powder. J. Agric. Food Chem., 42, 984–8.Google Scholar
  228. Slade, L. and Levine, H. (1991) A food polymer science approach to structure-property relationships in aqueous food systems: non-equilibrium behaviour of carbohydrate-water systems, in Water Relationships in Foods, ( H. Levine and L. Slade, eds.), Plenum Press, New York, pp. 29–101.Google Scholar
  229. Slade, L. and Levine, H. (1991) Beyond water activity: recent advances based on an alternative approach to the assessment of food quality and safety. Crit. Rev. Food Sci. Nutr., 30, 115–360.Google Scholar
  230. Smith, G.A. and Friedman, M. (1984) Effect of carbohydrate and heat on the amino acid composition and chemically available lysine content of casein. J. Food Sci., 49, 817–20.Google Scholar
  231. Smith, J.L. and Yada, R.Y. (1991) Chemical modification of amino groups in Mucor miehei aspartyl proteinase, porcine pepsin and chymosin. II. Conformational stability. Agric. Biol. Chem., 55, 2017–24.Google Scholar
  232. Smith, J.L., Billings, G.E. and Yada, R.Y. (1991) Chemical modification of amino groups in Mucor miehei aspartyl proteinase, procine pepsin and chymosin. I. Structure and function. Agric. Biol. Chem., 55 2009–16.Google Scholar
  233. Speck, J.C. (1958) The Lobrey de Bruyn-Alberda van Ekenstein transformation. Adv. Carbohydr. Chem., 13, 63–103.Google Scholar
  234. Srinivasan, A. and Gopalan, S. (1994) Influence and impact of non-enzymatic browning reaction on protein in milk and in indigenous dairy products of India, in Maillard Readctions in Chemistry, Food and Health, ( T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, p. 419.Google Scholar
  235. Stamp, J.A. and Labuza, T.P. (1983) Kinetics of the Maillard reaction between aspartame and glucose in solution at high temperatures. J. Food Sci., 48, 543–4, 547.Google Scholar
  236. Sullivan, J.F. (1981) Control of non-enzymatic browning in the dehydration of fruits and vegetables. Prog. Food Nutr. Sci., 5, 377–93.Google Scholar
  237. Sweetsur, A.W.M. and White, J.C.D. (1975) Studies on the heat stability of milk protein. III. Effect of heat-induced acidity in milk. J. Dairy Res., 42, 73–88.Google Scholar
  238. Tamura, Y., Mizota, T., Shimamura, S. and Tornita, M. (1993) Lactulose and its application to the food and pharmaecutical industries, Bulletin 289, International Dairy Federation, Brussels, pp. 43–53.Google Scholar
  239. Troyano, E., Martinez-Castro, I. and Olano, A. (1992b) Kinetics of galactose and tagatose formation during heat-treatment of milk. Food Chem., 45, 41–3.Google Scholar
  240. Troyano, E., Olano, A. and Martinez-Castro, I. (1994) Changes in free mono- saccharides during storage of dried milk. J. Agric. Food Chem., 42, 1543–5.Google Scholar
  241. Troyano, E., Olano, A., Jimeno, M.L., et al. (1992a) Isolation and characterization of 3-deoxypentosulose and its determination in heated milk. J. Dairy Res., 59, 507–15.Google Scholar
  242. Tsuchiya, S., Sakurai, T. and Sekiguchi, S.-I. (1984) Non-enzymatic glucosylation of human albumin and its influence on binding capacity on sulfonylureas. Biochem. Pharmacol., 33 2967–71.Google Scholar
  243. Tu, D., Xue, S., Meng, C., et al. (1992) Simultaneous determination of 2-furfuraldehyde and 5-(hydroxymethyl)-2-furfuraldehyde by derivative spectrophotometry. J. Agric. Food Chem., 40, 1022–5.Google Scholar
  244. Turner, L.G., Swaisgood, H.E. and Hansen, A.P. (1978) Interaction of lactose and proteins of skim milk during ultra-high temperature processing. J. Dairy Sci., 61, 384–92.Google Scholar
  245. Urashima, T., Suyema, K. and Adachi, S. (1988) The condensation of 5-(hydroxymethyl)-2-furaldehyde with some aldoses on heating. Food Chem., 29, 717.Google Scholar
  246. van Boekel, M.A.J.S. and Rehman, Z. (1987) Determination of hydroxymethylfurfural in heated milk by high performance liquid chromatography. Neth. Milk Dairy J., 41, 297–306.Google Scholar
  247. van Boekel, M.A.J.S. and Walstra, P. (1989) General introduction to kinetics, in Heat-Induced Changes in Milk, (P.F. Fox, ed.), Bulletin 238, International Dairy Federation, Brussels, pp. 3–12.Google Scholar
  248. Verhaar, L.A.Th., van der Aalst, M.J.M., Beenackers, J.A.W.M. and Kuster, B.F.M. (1979) Ion-exchange chromatography of lactose — lactulose isomerization mixtures using a boric acid-borate eluent. J. Chromatogr., 170, 363–70.Google Scholar
  249. Venkatachalam, N., McMahon, D.J. and Savello, P.A. (1993) Role of protein and lactose interactions in the age gelation of ultra-high temperature processed concentrated skim milk. J. Dairy Sci., 76, 1882–94.Google Scholar
  250. Vogel, J., Westphal, G. and Pippig, C. (1988) Mutarotation of D-glucose in dependence on the reaction environment. Nahrung, 32, 709–14.Google Scholar
  251. Walstra, P. and Jenness, R. (1984) Dairy Chemistry and Physics, John Wiley and Sons Inc., New York.Google Scholar
  252. Warmbier, H.C., Schnickels, R.A. and Labuza, T.P. (1976) Effect of glycerol on non-enzymatic browning in a solid intermediate moisture model food system. J. Food Sci., 41, 528–31.Google Scholar
  253. Weenan, H. and Tjan, S.B. (1992) Analysis structure and reactivity of 3-deoxyglucosone, in Flavour Precursors. Thermal and Enzymatic Conversions, ( R. Teranishi, G.R. Takeoka and M. Guntert, eds.), American Chemical Society, Washington, DC, pp. 217–31.Google Scholar
  254. Wertheim, J.H., Procter, B.E. and Goldblith, S.A. (1956) Radiation preservation of milk and milk products. IV. Radiation-induced browning and some related chemical changes in milk. J. Dairy Sci., 39, 1236–46.Google Scholar
  255. Westphal, G., Kroh, L. and Follmer, U. (1988) Investigations on the Maillard reaction. Part 16. The reactivity of Amadori compounds in dependence on the reaction medium. Nahrung, 32, 117–20.Google Scholar
  256. Wolf, J.C., Thompson, D.R. and Reineccius, G.A. (1977) Initial losses of available lysine in model systems. J. Food Sci., 42, 1540–4.Google Scholar
  257. Wolf, J.C., Warthesen, J.J., Thompson, D.R. and Reineccius, G.A. (1981) Mathematical model for predicting free lysine and methionine losses during thermal processing of fortified foods. Prog. Food Nutr. Sci., 5, 405–13.Google Scholar
  258. Wu, H., Govindarajan, S., Smith, T., et al. (1990) Glucose-lysozyme reactions in a restricted water environment, in The Maillard Reaction in Food Processing, Human Nutrition and Physiology, ( P.A. Finot, H.U. Aeschbacher, R.F. Hurrell and R. Liardon, eds.), Birkhäuser Verlag, Basel, pp. 85–90.Google Scholar
  259. Yang, R. and Shin, D.B. (1980) Study on the amino-carbonyl reaction. Korean J. Food Sci. Technol., 12, 88–96.Google Scholar
  260. Yaylayan, V. (1990) In search of alternative mechanisms for the Maillard reaction. Trends Food Sci. Technol., 1, 20–2.Google Scholar
  261. Yaylayan, V.A. and Forage, N.G. (1991) Determination of the kinetics and mechanism of decomposition of tryptophan Amadori rearrangement product by RP-HPLC analysis. J. Agric. Food Chem., 39, 364–9.Google Scholar
  262. Yaylayan, V.A. and Forage, N.G. (1992) A kinetic model for the reaction of tryptophan with glucose and mannose — the role of diglycation in the Maillard reaction. Food Chem., 44, 201–8.Google Scholar
  263. Yaylayan, V.A. and Huyghues-Despointes, A. (1994) Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions, spectroscopic properties. Crit. Rev. Food Sci. Nutr., 34, 321–69.Google Scholar
  264. Yaylayan, V.A. and Lachambre, S. (1990) Pyrylium betaines as reactive intermediates in Maillard reaction. J. Food Sci., 55, 1124–6.Google Scholar
  265. Yaylayan, V.A. and Mandeville, S. (1994) Mechanistic pathway for the formation of maltoxazine from intact 1-[2’-carboxyl)pyrrolidinyl]-1-deoxy-D-fructose (Amadori-Proline). J. Agric. Food. Chem., 42, 1841–4.Google Scholar
  266. Yen, G.C. and Lee, T-C. (1986) Mutagen formation in the reaction of Maillard browning products, 2-acetylpyrrole and its analogues, with nitrite. Food Chem. Toxicol., 24, 1303–8.Google Scholar
  267. Yoshimura, J., Funabashi, M. and Simon, H. (1969) On the catalysis of the Amadori rearrangement. Carbohydr. Res., 11, 276–81.Google Scholar
  268. Zyzak, D.V., Wells-Knecht, K.J., Blackledge, J.A., et al. (1994) Pathways of the Maillard reaction in vitro and in vivoin Maillard Reactions in Chemistry, Food and Health, (T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O’Brien and J.W. Baynes, eds.), Royal Society of Chemistry, Cambridge, pp. 274–80.Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1997

Authors and Affiliations

  • J. O’Brien

There are no affiliations available

Personalised recommendations