Oxidation of Free Tryptophan and Tryptophan Residues in Peptides and Proteins

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 2, 1998, Pages 490-498

  Simat, T J ^a   Steinhart, H ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Enzymatic hydrolysis; High performance liquid chromatography (HPLC); L Tryptophan; Oxidation

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

EID: 0000217491     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970818c     Document Type: Article

References (40)

1. BGVV (Bundesinstitut für gesundheitlichen Verbraucherschutz und Veterinärmedizin). 49.07-2: Bestimmung des Aminosäuregehaltes in diätetischen Lebensmitteln auf der Basis von Proteinhydrolysaten. In Amtliche Sammlung von Untersuchungsverfahren nach § 35 LMBG; Beuth Verlag GmbH: Berlin, 1986.
2. BGVV (Bundesinstitut für gesundheitlichen Verbraucherschutz und Veterinärmedizin). 49.07-3: Bestimmung des Tryptophangehaltes in diätetischen Lebensmitteln auf der Basis von Proteinhydrolysaten. In Amtliche Sammlung von Untersuchungsverfahren nach § 35 LMBG; Beuth Verlag GmbH: Berlin, 1989.
3. Chin, C. C. Q.; Wold, F. The Preparation of Matrix-Bound Proteases and Their Use in the Hydrolysis of Proteins. Anal. Biochem. 1974, 61, 379-391.
4. Chin, C. C. Q.; Wold, F. Enzymatic Hydrolysis of Native, Soluble Proteins and Glycoproteins. Methods Enzymol. 1984, 106, 69-74.
5. Cuq, J, C.; Cheftel, J. C. Tryptophan Degradation During Heat Treatments: Part 1-The Degradation of Free Tryptophan. Food Chem. 1983, 12, 1-14.
6. Cuq, J. C.; V́ie, M.; Cheftel, J. C. Tryptophan Degradation During Heat Treatments: Part 2-Degradation of Protein-Bound Tryptophan. Food Chem. 1983, 12, 73-88.
7. Elderfield, A. J.; Truscott, R. J. W. Is an Altered Tryptophan Metabolism Responsible for Age-Related Cataract? In Recent Advances in Tryptophan Research-Tryptophan and Serotonine Pathways; Allegri Filippini, G., Costa, C. V. L., Bertazzo, A., Eds.; Plenum Press: New York, 1996.
8. Finlayson, A. J. The Perfomic Acid Oxidation of Egg-White Lysozyme. Can. J. Biochem. 1969, 47, 31-37.
9. Garcia, S. E.; Baxter, J. H. Determination of Tryptophan Content in Infant Formulas and Medical Nutritionals. J. Assoc. Off. Anal. Chem. 1992, 75, 1112-1119.
10. Hauck, M. Enzymatische Hydrolyse von Proteinen zur Aminosäurebestimmung und Probenvorbereitung. Dtsch. Lebenm.-Rundsch. 1990, 86, 12-15.
11. Holt, L. A.; Milligan, B.; Rivett, D. E.; Stewart, F. H. C. The Photodecomposition of Tryptophan Peptides. Biochim. Biophys. Acta 1977, 499, 131-138.
12. Itakura, K.; Uchida, K.; Kawakishi, S. Selective Formation of Oxindole- and Formylkynurenine-Type Products from Tryptophan and its Peptides Treated with a Superoxide-Generating System in the Presence of Iron(III)-EDTA: A Possible Involvement with Iron-Oxygen Complex. Chem. Res. Toxicol. 1994, 7, 185-190.
13. Kanner, J. D.; Fennema, O. Photooxidation of Tryptophan in the Presence of Riboflavin. J. Agric. Food Chem. 1987, 35, 71-76.
14. 2 in Model Systems. J. Food Sci. 1990, 55, 1120-1123.
15. Kim, H.-J.; Haering, C. Evaluation of Protein Cross-Linking and Biodegradability by Determination of Tryptophan Released by Pronase Using Reversed-Phase HPLC with Photodiode Array Detection. J. Agric. Food Chem. 1994, 42, 915-918.
16. Krogull, M. K.; Fennema, O. Oxidation of Tryptophan in the Presence of Oxidizing Methyl Linoleate. J. Agric. Food Chem. 1987, 35, 66-70.
17. Labroo, R. B.; Cohen, L. A. Preparative Separation of the Diastereomers of Dioxindolyl-L-alanine and Assignment of Stereochemistry at C-3. J. Org. Chem. 1990, 55, 4901-4904.
18. Lee, M. G.; Rogers, C. M. Degradation of Tryptophan in Aqueous Solution. J. Parenter. Sci. Technol. 1988, 42, 20 22.
19. Matoba, T.; Yonezawa, D.; Nair, B. M.; Kito, M. Damage of Amino Acid Residues of Proteins after Reaction with Oxidizing Lipids: Estimation by Proteolytic Enzymes. J. Food Sci. 1984, 49, 1082-1084.
20. Nakagawa, M.; Kato, S.; Kataoka, S.; Kodato, S; Watanabe, H.; Okajima, H.; Hino, T.; Witkop, P. Dye-sensitized Photooxygenation of Tryptophan: 3a-Hydroperoxypyrroloindole as a Labile Precursor of Formylkynurenine. Chem. Pharm. Bull. 1981, 29, 1013-1026.
21. Narahashi, Y.; Yanagita, M. Studies on Proteolytic Enzymea (Pronase) of Streptomyces griseus K-1-1. Nature and Properties of the Proteolytic Enzyme System. J. Biochem. 1967, 62, 633-641.
22. Nielsen, H. K.; Weck, D. de; Finot, P. A.; Liardon, R.; Hurrell, R. F. Stability of Tryptophan During Food Processing and Storage. 1. Comparative Losses of Tryptophan, Lysine and Methionine in Different Model Systems. Br. J. Nutr. 1985a, 53, 281-292.
23. Nielsen, H. K.; Finot, P. A.; Hurrell, R. F. Reactions of Proteins with Oxidizing Lipids. 2. Influence on Protein Quality and on the Bioavailability of Lysine, Methionine, Cyst(e)ine and Tryptophan as Measured in Rat Assays. Br. J. Nutr. 1985b, 53, 75-86.
24. Nielsen, H. K.; Klein A.; Hurrell R. F. 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. 1985c, 53, 293-300.
25. Nielsen, H. K.; Löliger, J.; Hurrell, R. F. 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. 1985d, 53, 61-73.
26. Okajima, T.; Kawata, Y.; Hamaguchi, K. Chemical Modification of Tryptophan Residues and Stability Changes in Proteins. Biochemistry 1990, 29, 9168-9175.
27. Röper, K.; Föhles, J.; Klostermeyer, H. Complete Enzymatic Hydrolysis of Wool and Its Morphological Components. Methods Enzymol. 1984, 706, 58-69.
28. Savige, W. E. New Oxidation Products of Tryptophan. Aust. J. Chem. 1975, 28, 2275-2287.
29. Savige, W. E.; Fontana, A. New Procedure for Oxidation of 3-Substituted Indoles to Oxindoles: Modification of Tryptophan Residues in Peptides and Proteins. J. Chem. Soc., Chem. Commun. 1976, 599-600.
30. Schmitz, I.; Zahn, H.; Klostermeyer, H.; Rabbel, K.; Watanabe, K. Zum Vorkommen von Isopeptidbindungen in erhitztem Milcheiweiss. Z. Lebensm. Unters. Forach. 1976, 160, 377-381.
31. Simat, T.; Meyer, K.; Steinhart, H. Synthesis and Analysis of Oxidation and Carbonyl Condensation Compounds of Tryptophan. J. Chromatogr. A 1994, 661, 93-99.
32. Simat, T.; van Wickern, B.; Eulitz, K.; Steinhart, H. Contaminants in Biotechnologically Manufactured L-Tryptophan. J. Chromatogr. B 1996, 685, 41-51.
33. Snell, E. E. Tryptophanase: Structure, Catalytic Activities, and Mechanism of Action. Adv. Enzymol. Relat. Areas Mol. Biol. 1975, 42, 287-333.
34. Steinhart, H. Stability of Tryptophan in Peptides against Oxidation and Irradiation. In Kynurenine and Serotonine Pathway s-Progress in Tryptophan Research; Schwarcz, R., Young, S. N., Brown, R. R., Eds.; Plenum Press: New York, 1991.
35. 2. J. Agric. Food Chem. 1993, 41, 2275-2277.
36. Uchida, K.; Kawakishi, S. Selective Oxidation of Tryptophan and Histidin Residues in Protein through the Coppercatalyzed Autoxidation of L-Ascorbic Acid. Agric. Biol. Chem. 1988, 52, 1529-1535.
37. Uchida, K.; Enomoto, N.; Itakura, K.; Kawakishi, S. Formation of Diastereomeric 3a-Hydroxypyrroloindoles from a Tryptophan Residue Analog Mediated by Iron(II)-EDTA and L-Ascorbate. Arch. Biochem. Biophys. 1990, 279, 14-20.
38. Weck, D. de; Nielsen, H. K.; Finot, P.-A. Oxidation Rate of Free and Protein-Bound Tryptophan by Hydrogen Peroxide and the Bioavailability of the Oxidation Products. J. Sci. Food Agric. 1987, 41, 179-185.
39. Wickern, B. van; Kleeberg, K.; Rogosch, D.; Steinhart, H. Oxidation of γ-Irradiation Induced Products in Free and Peptide Bound Tryptophan. In Recent Advances in Tryptophan Research-Tryptophan and Serotonine Pathways; Allegri Filippini, G., Costa, C. V. L., Bertazzo, A., Eds.; Plenum Press: New York, 1996.
40. Yong, S. H.; Lau, S.; Hsieh, Y.; Karel, M. Degradation Products of L-Tryptophan Reacted with Peroxidizing Methyl Linoleate. In Autoxidation in Food and Biological Systems; Simic, M. G., Karel, M., Eds.; Plenum Press: New York 1980.