Convenient synthesis of lactuloselysine and its use for LC-MS analysis in milk-like model systems

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 11, 1999, Pages 4700-4706

  Vinale, Francesco ^a   Monti, Simona Maria ^a   Panunzi, Barbara ^a   Fogliano, Vincenzo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Lactuloselysine; LC MS; Maillard reaction; Milklike model systems

Indexed keywords

DRUG DERIVATIVE; EPSILON-N-1-(1-DEOXYLACTULOSYL)LYSINE; LACTOSE; LACTULOSE; LACTULOSELYSINE; MILK; MILK PROTEIN; PROTEIN; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG; WHEY PROTEIN;

ANIMAL; ARTICLE; CHEMICAL REACTION; CHEMISTRY; FOOD PROCESSING; FOOD QUALITY; GLYCATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MODEL; NUTRITIONAL VALUE; SYNTHESIS;

ANIMALS; CHROMATOGRAPHY, LIQUID; LACTULOSE; MASS SPECTROMETRY; MILK; MILK PROTEINS; MODELS, CHEMICAL;

EID: 0033230062     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990237i     Document Type: Article

References (27)

1. Aschaffenburg, R.; Dewry, J. New procedure for routine determination of various noncasein proteins of milk. 15th Int. Dairy Congr. Lond. 1959, 3, 1631-1637.
2. Badoud, R.; Fay, L.; Richli, U.; Husek, P. Gas-chromatography determination of N-carboxymethyl amino acids, the periodate oxidation products of Amadori compounds. J. Chromatogr. 1991, 552, 345-351.
3. Berg, H. E.; Van Boekel, M. A. J. S. Degratation of lactose during heating of milk. 1 Reaction pathways. Netherland Milk Dairy J. 1994, 48, 157-175.
4. Burton, H. Reviews of the progress of dairy science. The bacteriological, chemical, biochemical and physical changes that can occur in milk at temperatures of 100-150°C. J. Dairy Res. 1984, 51, 341-363.
5. Carpino, L. A.; Han, G. Y. The 9-fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 1972, 37, 3404-3409.
6. Corradini, C. Le proteine. In Chimica e tecnologia del latte; Tecniche nuove ed.; Milano, Italia, 1995.
7. Erbersdobler, H. F. Twenty years of furosine - better knowledge about the biological significance of Maillard reaction in food and nutrition. Proceedings of the 3rd International Symposium on the Maillard reaction: "Amino-Carbonyl Reaction in Food and Biological systems" Fuji Institute, Japan 1985; Fujimaki, M., Namiki, M., Kato, H, Eds.; Elsevier Science Publishers: Amsterdam, and Kodansha Ltd.: Tokyo, 1986; Development in Food Science, Vol. 13, pp 481-491.
8. Erbersdobler, H. F. Twenty years of furosine - better knowledge about the biological significance of Maillard reaction in food and nutrition. Proceedings of the 3rd International Symposium on the Maillard reaction: "Amino-Carbonyl Reaction in Food and Biological systems" Fuji Institute, Japan 1985; Fujimaki, M., Namiki, M., Kato, H, Eds.; Elsevier Science Publishers: Amsterdam, and Kodansha Ltd.: Tokyo, 1986; Development in Food Science, Vol. 13, pp 481-491.
9. Finot, P. A. Metabolism and physiological effects of Maillard reaction products. In The Maillard reaction in Food Processing, Human Nutrition and Physiology; Finot, P. A., Aeschbacher, H., Hurrel, R. F., Liardon, R., Eds.; Birgansen Verlang: Basel, 1990.
10. Finot, P. A.; Deutsch, R.; Bujard, E. The exent of the Maillard reaction during the processing of milk. Prog. Fd. Nutr. Sci. 1981, 5, 345-355.
11. Finot, P. A.; Mauron, J. Le blocage de la lysine par la réaction de Maillard. I. Synthèse de N-(désoxy-1-D-fructosil-1-) et N-(désoxy-1-D-lactulosil-1-)-L-lysine. Helv. Chim. Acta 1969, 52, 1488-1495.
12. Fogliano, V.; Monti, S. M.; Ritieni, A.; Marchisano, C.; Peluso, G.; Randazzo, G. An immunological approach to monitor protein lactosylation of heated food model system. Food Chem. 1997, 58, 53-58.
13. Friedmann, M. Food brownig and its prevention: an overview. J. Agric. Food. Chem. 1996a, 44, 631-653.
14. Friedmann, M. The impact of the Maillard reaction on the nutritional value of food proteins. In The Maillard Rection: Conseguences for the Chemical and Life Sciences; Ihan, R., Ed.; Wiley and Sons: New York, 1996b.
15. Furth, A. J. Methods for assaying nonenzymatic glycosylation. Analit. Biochem. 1988, 175, 347-360.
16. Henle, T.; Walter, H.; Klostermeyer, H. Evalutation of the extent of the early Maillard-reaction in milk products by direct measurement of the Amadori-product lactuloselysine. Z. Lebensm. Unters. Forsch. 1991, 193, 119-122.
17. Mauron, J. The Maillard reaction in food: a critical review from the nutritional standpoint. Prog. Fd. Nutr. Sci. 1981, 5, 5-35.
18. Monti, S. M.; Bailey, R. G.; Ames, J. M. The influence of pH on the non-volatile reaction products of aqueous Maillard model systems by HPLC with diode array detection. Food Chem. 1998, 62, 369-375.
19. Monti, S. M.; Ritieni A.; Graziani, G.; Randazzo, G.; Mannina, L.; Segre, A. L.; Fogliano, V. LC-MS analysis and antioxidative efficiency of Maillard reaction products from a lactose-lysine model system. J. Agric. Food. Chem. 1999, 47, 1506-1513.
20. Morales, F. J.; Jemenez Perez, S. Study of HMF formed from acid degradation of the A.P. in milk resembling system. J. Agric. Food. Chem. 1998, 46, 3885-90.
21. Olano, A.; Santa-Maria, G.; Corzo, N.; Calvo, M. M.; Martines-Castro, I.; Jimeno, M. L. Determination of free carbohydrates and Amadori compounds formed at the early stages of nonenzymic browning. Food Chem. 1992, 43, 351-358.
22. Pellegrino, L.; Resmini, P.; Luf, W. Assestement (indices) of heat treatment of milk. In Heat-induced Changes in Milk: Fox, P. F., Ed.; International Dairy Federation: Brussels. 1995.
23. Pizzano, R.; Nicolai, M. A.; Siciliano, R.; Addeo, F. Specific deletion of the Amadori compounds in milk by using polyclonal antibodies raised against a lactosylated peptide. J. Agric. Food Chem. 1998, 46, 5373-5379.
24. Porretta, S. Chromatographic analysis of Maillard reaction products. J. Chromatogr. 1992, 624, 211-219
25. Resmini, P.; Pellegrino, L.; Batelli, G. Accurate quantification of furosine in milk and dairy products by a direct HPLC method. Italian J. Food Sci. 1990, 3, 173-183.
26. Schreuder, H. A.; Welling, G. W. Determination of β-galactosidase activity in the intestinal tract of mice by ion-exchange high-performance liquid chromatography using ∈-N-1-(1-deoxylactulosil)-L-lysine as substrate. J. Chromatoer. 1983 278, 275-282.
27. van Boekel, M. A. J. S. Effect of heating on Maillard reactions in milk. Food Chem. 1998, 62, 403-414.