Optimization of the synthesis of the cross-linked amino acid ornithinoalanine and nuclear magnetic resonance characterization of lysinoalanine and ornithinoalanine

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 3, 1999, Pages 939-944

  Boschin, Giovanna ^a   Scaglioni, Leonardo ^a   Arnoldi, Anna ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Diastereoisomers; Lysinoalanine; NMR analysis; Ornithinoalanine; Synthesis

Indexed keywords

ALANINE; AMINO ACID; CROSS LINKING REAGENT; DIPEPTIDE; LYSINOALANINE; ORNITHINE; ORNITHINOALANINE;

ALKALINITY; AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; COOKING; CROSS LINKING; FOOD; FOOD HANDLING; NEPHROTOXICITY; NUCLEAR MAGNETIC RESONANCE; NUTRITION; STEREOISOMERISM; SYNTHESIS;

ALANINE; COOKERY; CROSS-LINKING REAGENTS; DIPEPTIDES; FOOD HANDLING; LYSINOALANINE; MAGNETIC RESONANCE SPECTROSCOPY; ORNITHINE;

EID: 0032912491     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980869p     Document Type: Article

References (32)

1. Bax, A.; Morris, G. A. An improved method for heteronuclear chemical shift correlation by two-dimensional NMR. J. Magn. Reson. 1981, 42, 501-505.
2. 13C assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 1986, 108, 2093-2094.
3. Büser, W.; Erbersdobler, H. F. Gaschromatographische Aminosäurenbestimmung mit stickstoffeselektiver Detektion (Gas chromatographic amino acid determination with nitrogen dectection). Z. Lebensm. Unters. Forsch. 1988, 186, 509-513.
4. Cecchi, L.; Resmini, P. Degradation of arginine in gorgonzola cheese. III. Influence of various microorganisms. Latte 1973, 391-394.
5. Collar, C.; Mascaros, A. F.; Prieto, J. A.; Benedito de Barber, C. Changes in free amino acids during fermentation of wheat doughs started with pure culture of lactic acid bacteria. Cereal Chem. 1991, 68, 66-72.
6. de Koning, P. J.; van Rooijen, P. J. Aspects of the formation of lysinoalanine in milk and milk products. J. Dairy Res. 1982, 49, 725-736.
7. de Weck-Gaudard, D.; Liardon, R.; Finot, P. A. Stereomeric composition of urinary lysinoalanine after ingestion of free or protein-bound lysinoalanine in rats. J. Agric. Food Chem. 1988, 36, 717-721.
8. Febrer, M. A.; Mirò, P. A new synthesis of ornithinoalanine. Invest. Inform. Text. 1969, 12, 293-296.
9. Friedman, M.; Liardon, R. Racemization kinetics of amino acid residues in alkali-treated soybean proteins. J. Agric. Food Chem. 1985, 33, 666-672.
10. Friedman, M.; Pearce, K. N. Copper(II) and cobalt(II) affinities of LL- and LD-Lysinolanine diastereomers: implications for food safety and nutrition. J. Agric. Food Chem. 1989, 37, 123-127.
11. Friedman, M.; Gumbmann, M. R.; Masters, P. M. Protein-alkali reactions: chemistry, toxicology, and nutritional consequences. Adv. Exp. Med. Biol. 1984, 177, 367-412.
12. Hasegawa, K.; Iwata, S. Gas chromatography-mass spectrometry of lysinoalanine and the related cross linked amino acids in alkali treated food proteins. Agric. Biol Chem. 1982, 46, 2513-2520.
13. Hasegawa, K.; Mukai, K.; Gotoh, M.; Honjo, S.; Matoba, T. Determination of lysinoalanine content in commercial foods by gas chromatography selected ion monitoring. Agric. Biol. Chem. 1987, 51, 2889-2894.
14. Hellmann, H.; Teichmann, K.; Lingens, F. α-Acylaminoacrylester aus α-Acylaminomalonestern. Chem. Ber. 1958, 91, 2427-2431.
15. π-(2′-amino-2′-carboxyethyl)-L-histidine ("histidinoalanine", HAL) in heated milk products. Z. Lebensm. Unters. Forsch. 1993, 197, 114-117.
16. Henle, T.; Schwarzenbolz, U.; Klostermeyer, H. Irreversible cross-linking of casein during storage of UHT-treated skim milk. Heat Treatments and Alternative Methods; Special Issue 9602; International Dairy Federation: Brussels, Belgium, 1996; pp 290-298.
17. Jonker, D.; Woutersen, R. A.; Feron, V. J. Toxicity of mixtures of nephrotoxicants with similar or dissimilar mode of action. Food Chem Toxicol. 1996, 34, 1075-1082.
18. Ledger, R.; Stewart, F. H. C. The use of sequestering agents in the preparation of ∈-acyl-L-lisine and δ-acyl-L-ornithine derivatives. Aust. J. Chem. 1965, 18, 933-935.
19. Liardon, R.; Friedman, M.; Philippossian, G. Racemization kinetics of free and protein-bound lysinoalanine (LAL) in strong acid media. Isomeric composition of bound LAL in processed proteins. J. Agric. Food Chem. 1991, 39, 531-537.
20. Maga, J. A. Lysinoalanine in foods. J. Agric. Food Chem. 1984, 32, 955-964.
21. Mirò, P.; Puente, J.; Anguera, S.; Febrer, M. A. A new amino acid: ornithinoalanine. Synthesis and isolation in wool treated with sodium hydroxide. Invest. Inform. Text. 1968, 11, 471-78.
22. Moret, S.; Cherubin, S.; Rodriguez-Estrada, M. T.; Lercker, G. Determination of lysinoalanine by high performance liquid chromatography. J. High Resolut. Chromatrogr. 1994, 17, 827-830.
23. Pellegrino, L.; Resmini, P.; De Noni, I.; Masotti, F. Sensitive determination of lysinoalanine for distinguishing natural from imitation mozzarella cheese. J. Dairy Sci. 1996, 79, 725-734.
24. Pellegrino, L.; van Boekel, M. A. J. S.; Gruppen, H.; Resmini, P. Maillard compounds as crosslinks in heated β-casein-glucose systems. In The Maillard Reaction in Food and Medicine; O'Brien, J., Nursten, H. E., Ames J. M., Eds.; The Royal Society of Chemistry, Cambridge, U.K., 1998; pp 100-101.
25. Pintauro, S. J.; Philipossian, G.; Finot, P. A.; Lee, T. C. Lysinoalanine: absence of mutagenic response in the Salmonella/mammalian-microsome mutagenicity assay. Food Chem. Toxicol. 1985, 23, 763-765.
26. Savoie, L.; Parent, G.; Galibois, I. Effects of alkali treatment on the in-vitro digestibility of proteins and the release of amino acids. J. Sci. Food Agric. 1991, 56, 363-372.
27. Tas, A. C.; Kleipool R. J. C The stereoisomers of lysinoalanine. Lebensm. Wiss. Technol. 1976, 9, 360-362.
28. Walter, A. W.; Henle, T.; Haessner, R.; Klostermeyer, H. Studies on the formation of lysinomethylalanine and histidinomethylalanine in milk products. Z. Lebensm. Unters. Forsch. 1994, 199, 243-247.
29. Warthesen, J. J.; Wood-Rethwill, J. Lysinoalanine in foods as measured via dansylderivative. CRC Handbook of HPLC Separation of Amino Acids, Peptides, and Proteins. Vol. 1; Hancock, W. S., Ed.; CRC Press: Boca Raton, FL, 1984; pp 351-357.
30. Wolf, D. E.; Valiant, J.; Peck, R. L.; Folkers, K. Synthesis of Biocytin. J. Am. Chem. Soc. 1952, 74, 2002-2003.
31. Wood-Rethwill, J. C.; Warthesen, J. J. Lysinoalanine determination in proteins using high-pressure liquid chromatography. J. Food Sci. 1980, 45, 1637-1640.
32. Ziegler, K.; Melchert, I.; Lürken, C. Nδ-(2-amino-2-carboxyethyl)-ornithine, a new amino acid from alkali-treated proteins. Nature 1967, 214, 404-405.