Abstract
Proteins may be exposed to a variety of oxidizing conditions during food processing and storage. Examples of deliberate oxidation are the addition of bromate, acetone peroxide or benzoyl peroxide to improve dough strength in the baking industry and the direct addition of hydrogen peroxide for bleaching or preservation elsewhere in the food industry (1). However, the most common oxidizing agents are lipid hydroperoxides. Urbanization of society has necessitated increased processing, shipping and storage of food products, all of which increase the likelihood of lipid hydroperoxide formation and possible development of off-flavors and odors. In protein foods containing polyunsaturated lipids, there is the additional risk of lipid hydroperoxide-induced oxidation of proteins and, more specifically, the sulfur amino acids of proteins. The oxidative changes in amino acids have been previously reviewed extensively (2,3,4,5,6). Significant nutritional losses have been reported in proteins which have been exposed to either hydrogen peroxide or oxidizing lipids (7,8).
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
P. Slump and H. A. W. Schreuder, Oxidation of Methionine and Cystine in Foods Treated with Hydrogen Peroxide, J. Sci. Food Agric. 24: 657–661 (1973).
Y. M. Torchinskii, Sulfhydryl and Disulfide Groups of Proteins (Translated by H. B. F. Dixon ), Consultants’ Bureau, New York (1973).
P. C. Jocelyn, Biochemistry of the SH Group, Academic Press, New York (1972).
M. Friedman, Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids and Proteins. Pergamon Press, New York (1973).
H. W. Gardner, Lipid Hydroperoxide Reactivity with Proteins and Amino Acids: A Review, J. Agric. Food Chem. 27: 220–229 (1979).
H. G. Walker, G. O. Kohler, D. D. Kuzmicky and S. C. Witt, Problems in Analysis for Sulfur Amino Acids in Feeds and Foods. In: Protein Nutritional Quality of Foods and Feeds. Part 1. Ed. by M. Friedman and M. Dekker, Inc., New York (1975).
T. Horigome, T. Yanagida and M. Miura, Nutritive Value of Proteins Prepared by Reaction with Oxidized Ethyl Linoleate in Aqueous Medium, Nippon Nogei Kagaku Kaishi 43: 437 (1974).
L. B. Sjöberg and S. L. Boström, Studies in Rats on the Nutritional Value of Hydrogen Peroxide-Treated Fish Protein and the Utilization of Oxidized Sulfur Amino Acids, Br. J. Nutr. 38: 189–205 (1977).
C. Little and P. J. O’Brien, Products of Oxidation of a Protein Thiol Group after Reaction with Various Oxidizing Agents, Arch. Biochem. Biophys. 122: 406–410 (1967).
S. H. Lipton, C. E. Bodwell and A. H. Coleman, Jr., Amino Acid Analyzer Studies of the Products of Peroxide Oxidation of Cystine, Lanthionine and Homocystine.
S. E. Lewis and E. D. Wills, The Destruction of -SH Groups of Proteins and Amino Acids by Peroxides of Unsaturated Fatty Acids, Biochem. Pharmacol. 11: 901–912 (1962).
H. W. Gardner, R. Kleiman, D. Wersleder and G. E. Inglett, Cysteine Adds to Lipid Hydroperoxide, Lipids 12: 655 (1977).
H. W. Gardner, D. Wesleder, and R. Kleiman, Addition of N-Acetyl-Cysteine to Linoleic Acid Hydroperoxide, Lipids 11: 127 (1976).
M. Karel, K. Schaich, and B. R. Roy, Interaction of Peroxidizing Methyl Linoleate with Some Proteins and Amino Acids, J. Agric. Food. Chem. 23: 158 (1975).
J. Kanner and M. Karel, Changes in Lysozyme Due to Reactions with Peroxidizing Methyl Linoleate in a Dehydrated Model System. J. Agric. Food Chem. 24: 460 (1968).
L6. K. Schaich and M. Karel, Free Radical Reactions of Peroxidizing Lipids with Amino Acids and Proteins, Lipids 11: 392 (1976).
M. A. Bennett, Metabolism of Sulfur V. The replaceability of L-cystine in the diets of rats with some partially oxidized derivatives, Biochem. J. 31B: 962–965 (1937).
A. J. Finlayson, S. Mackenzie and J. W. Finley, Reactions of Alanine-3-Sulfinic Acid with 2-liercapto Ethanol, Can. J. Chem. Accepted for publication 1980.
G. Axelson, K. hamrin, A. Fahlman, C. Nordling and B. J. Lindberg, Electron Spectroscopic Evidence of the Thiosulfonate Structure of Cystine S-dioxide. Spectrochin. Acta Part A 23: 2015–2020 (1967).
M. A. Bennett, Metabolism of Sulfur X. The replacement of DLmethionine in the diet of albino rats with its partially oxidized derivative DL-methionine sulfoxide, Biochem. J. 33: 1794–1797 (1939).
S. A. Miller, S. R. Tannenbaum and A. W. Seitz, Utilization of L-Methionine Sulfoxide by the Rat, J. Nutr. 100: 909 (1970).
G. M. Ellinger and R. Palmer, The Biological Availability of Methionine Sulfoxide, Proc. Nutr. Soc. 28: 42A (1969).
D. D. Kuzmicky, G. 0. Kohler, h. G. Walker, Jr. and b. E. Mackey, Availability of Oxidized Sulfur Amino Acids for the Growing Chick, Poultry Sci. 1560 (1970).
H. G. Anderson, D. M. V. Ashley and J. D. Jones, Utilization of L-Methionine Sulfoxide, L-Methionine Sulfone and Cysteic Acid by the Weanling Rat, J. Nutr. 106: 1108 (1976).
A. U. Gjoen and L. R. Njaa, Methionine Sulfoxide as a Source of Sulfur Containing Amino Acids for the Young Rat, Br. J. Nutr. 37: 93 (1977).
J. L. Cuq, P. Besancon, L. Chartier and P. Cheftel, Oxidation of Methionine Residues of Food Proteins and Nutritional Availability of Methionine Sulfoxide, Food Chess. 3:85–101 (197b).
L. B. Sjoberg and S. L. Bostrom, Studies in Rats on the Nutritional Value of hydrogen Peroxide-Treated Fish Protein and the Utilization of Oxidized Sulfur Amino Acids, Br. J. Nutr. 38: 189–205 (1977).
G. M. Ellinger, A Chemical Approach to the Nutritional Availability of Methionine in Proteins, Ann. Nutr. Alim. 32: 281–289 (1978).
J. L. Cuq, H. Provansal, L. Chartier, P. Besancon and C. Cheftel, Effects of Oxidative and Alfaline Treatments of Food Proteins on the Nutritional Availability of Methionine and Lysine, 111th International Congress of Food Science and Technology, Madrid (1974).
J. O. Anderson, R. H. Warnick and R. K. Dalai, Replacing Dietary Methionine and Cystine in Chick Diets with Sulfate and Other Sulfur Compounds, Poultry Sci. 54: 1122 (1975).
D. S. Miller and P. D. Samuel, Effects of the Addition of Sulfur Compounds to the Diet on Utilization of Protein in Young Growing Rats, J. Sci. Food Agric. 21:b1b (1970).
J. W. Finley, R. E. Lundin and A. J. Finlayson, A Study of the Oxidation of Cysteine Residues in Proteins and Peptides, Am. Chem. Soc. Annual Meeting, honolulu, Hawaii (1979).
J. W. Finley, H. G. Walker and E. L. Wheeler, Joint Meeting of the Americal Oil Chemists’ Soceity and Japan Oil Chemists’ Society, San Francisco, April 29 - May 3, 1979.
A. Allerhand, R. F. Childers and E. Ulfield, Natural-Abundance Carbon-13 Nuclear Magnetic Resonance Studies in 200 mm Sample Tubes. Observation of Numerous Single Carbon Resonance of hen Egg White Lysozyme, Biochemistry 12: 1335 (1973).
G. Jung, Fourier Transform 13C-NMR Spectroscopy of Biologically Active Cysteine Peptides, Angew Chem. 9: 894 (1970).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1980 Springer Science+Business Media New York
About this chapter
Cite this chapter
Finley, J.W., Lundin, R.E. (1980). Lipid Hydroperoxide Induced Oxidation of Cysteine in Peptides. In: Simic, M.G., Karel, M. (eds) Autoxidation in Food and Biological Systems. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9351-2_14
Download citation
DOI: https://doi.org/10.1007/978-1-4757-9351-2_14
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-9353-6
Online ISBN: 978-1-4757-9351-2
eBook Packages: Springer Book Archive