Oxidative Browning of Amadori Compounds from Amino Acids and Peptides
The oxygen-dependent browning (oxidative browning) of Amadori compounds from amino acids or peptides was studied since it was an important reaction contributing to the discoloration and deterioration of some foodstuffs containing sugars and amino compounds during storage in contact with atmospheric oxygen.
The browning of fourteen Amadori compounds derived from amino acids and peptides was determined under the influence of metals or oxygen. All Amadori compounds exhibited remarkable browning during storage at 37°C for 5 days when both 40 ppm of Fe2+and oxygen were present, but exhibited little browning without Fe2+or oxygen. Every mixture of a parent sugar and amino compound showed no browning even though Fe2+and oxygen were present. In particular, Amadori compounds composed of aromatic or heterocyclic amino acids were very reactive in oxidative browning, and this type of browning was synergistically accelerated by the presence of both Fe2+and Mn2+. The Amadori compound derived from pentose such as xylulose-glycine browned more rapidly than that from hexose such as fructose-glycine. Oxygen was thought to accelerate the breakdown of Amadori compounds to liberate parent amino acids and glucosone in the oxidative browning reaction.
In the browning reaction between glucose and seven peptides, glycylglycine, glycylleucine, leucylglycine, glycyltyrosine, glycylphenylalanine, glycylproline and glycylglycylglycine, the liberation of C-terminal amino acids by the cleavage of peptide bonds was observed. The amino acids were suggested to be liberated from the peptide in Amadori compounds, because the peptide bond in Amadori compounds was found to be more labile from the peptide.
KeywordsAmino Acid Analyzer Unknown Compound Amino Compound Browning Reaction Amadori Compound
Unable to display preview. Download preview PDF.
- Bayne, S., Methods Carbohydr. Chem. 2 421 (1963).Google Scholar
- Borsook, H., Natl. Acad. Sci.-Nati. Res. Council Publ. 557, 111 (1958).Google Scholar
- Clifcorn, L.E., Advan. Food Res. 1, 48 (1948).Google Scholar
- Coulter, S.T., Jenness, R., Geddes, W.F., Advan. Food Res. 3, 47 (1951).Google Scholar
- Davidson, S., Meiklejohn, A.P., Passmore, R., “Human Nutrition and Dietetics,” (1959), E. & S. Livingstone Ltd., Edinburgh & London, p. 179.Google Scholar
- Fox, B.A., Cameron, A.G.,“A Chemical Approach to Food and Nutrition”, (1961), University of London Press Ltd., p. 226.Google Scholar
- Hodge, J.E., J. Agric. Food Chem. 1 928 (1953).Google Scholar
- Hodge, J.E., Fisher, B.E., Methods Carbohydr. Chem. 2. 99 (1963).Google Scholar
- Hodge, J.E., Advan. Carbohydr. Chem. 10, 187 (1955).Google Scholar
- Horn, M.J., Lichtenstein, H., Womack, M., J. Agric. Food Chem. 16, 741 (1968).Google Scholar
- Kato, H., Sakurai, Y., Nippon Nogei Kagaku Kaishi 38, 536 (1964). Kato, H., Agric. Biol. Chem. 26, 187 (1962).Google Scholar
- Markuze, Z., Ghem. Abst. 59. 4980 (1963).Google Scholar
- Mitsuda,H., Shikanai,T., Vitamins (Japan) 13, 394 (1957).Google Scholar
- Nelson,N., J. Biol. Chem. 153, 375 (1944).Google Scholar
- Okuhara,A., Saito,N., Yokotsuka,T., J. Ferment. Technol. 49, 272 (1971).Google Scholar
- Omata,S., Ueno,T., Nakagawa,Y., Nippon Nogei Kagaku Kaishi 29, 259 (1955).Google Scholar
- Prey,V.V., Petershofer,G., Z. Zuckerind. 18. 63 (1968).Google Scholar
- Reynolds,T.M., Advan. Food Res. 14. 168 (1965).Google Scholar
- Sato,S., Tadenuma,M., Nippon Jozo Kyokai Zasshi 62. 1287 (1967).Google Scholar
- Somers,G.F., Beeson,K.C., Advan. Food Res. 1, 314 (1948).Google Scholar
- Takeuchi, T., J. Ferment. Technol. 54, 143 (1976).Google Scholar
- Ting,S.V., J. Agric. Food Chem. 4, 263 (1956).Google Scholar
- Yoda,A., J. Chem. Soc. Jap. 73, 18 (1952).Google Scholar