Reaction of L-Ascorbic Acid with L-Arginine Derivatives

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 8, 1996, Pages 2081-2085

  Pischetsrieder, Monika ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Ascorbic acid; L arginine; Maillard reaction

Indexed keywords

EID: 0001702307     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf960141d     Document Type: Article

References (27)

1. Bengelsdorf, I. Reaction of guanidine with glyoxals in aqueous solution-preparation of glycocyamidines. J. Am. Chem. Soc. 1953, 75, 3138.
2. Bensch, K.; Fleming, J.; Lohmann, W. The role of ascorbic acid in senile cataract. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7193-7196.
3. Duerksen-Hughes, P.; Williamson, M.; Wilkinson, K. Affinity chromatography using protein immobilized via arginine residues: purification of ubiquitin carboxyl-terminal hydrolases. Biochemistry 1989, 28, 8530-8536.
4. e-(carboxymethyl)lysine by reaction between lysine and products of autoxidation of ascorbate. Biochemistry 1990, 29, 10964-10970.
5. Edward, J.; Lantos, I. Solvent effects on the tautomeric equilibria of 4,4/5,5-disubstituted 4H/5H-imidazol-5/4-ones. J. Heterocycl. Chem. 1972, 9, 363 -369.
6. Henle, T.; Walter, A.; Haessner, R.; Klostermeyer, H. Detection and identification of a protein-bound imidalone resulting from the reaction of arginine residues and methylglyoxal. Z. Lebensm. Unters. Forsch. 1994, 199, 55-58.
7. Kirk, J. In Rockland, L., Stewart, G., Eds., Water activity: Influences on food quality; Academic Press: New York,1981; p 631.
8. Kurata, T.; Fujimaki, M.; Sakurai, Y. Red pigment produced by the reaction of dehydro-L-ascorbic acid with α-amino acid. Agric. Biol. Chem. 1973, 37, 1471-1477.
9. Lempert, C. The chemistry of the glycocyamidines. Chem. Rev. 1959, 59, 667-736.
10. Liao, M.; Seib, P. Selected reactions of L-ascorbic acid related to foods. Food Technol. 1987, 41 (11), 104-107.
11. Lo, T.; Westwood, M.; McLellan, A.; Selwood, T.; Thornally, P. Binding and modification of proteins by methylglyoxal under physiological conditions. J. Biol. Chem. 1994, 269, 32299-32305.
12. Nagy, S.; Lee, H.; Rouseff, R.; Lin, J. Nonenzymatic browning of commercially canned and bottled grapefruit juice. J. Agric. Food Chem. 1990, 38, 343-346.
13. Niemelä, K. Oxidative and non-oxidative alkali-catalysed degradation of L-ascorbic acid. J. Chromatogr. 1987, 399, 235-243.
14. Nishimura, T.; Kitajima, K. Novel synthesis of imidazole derivatives from 1-phenyl-1,2-propanedione and methylguanidine. J. Org. Chem. 1976, 41, 1590-1593.
15. Nishimura, T.; Nakano, K.; Shibamoto, S.; Kitajima, K. A novel synthesis of 2-(disubstituted amino)-5(4)-phenylimidazoles. J. Heterocycl. Chem. 1975, 12, 471-476.
16. Ortwerth, B.; Olesen, P. Ascorbic acid-induced crosslinking of lens proteins: evidence supporting a Maillard reaction. Biochim. Biophys. Acta 1988, 956, 10-22.
17. Ortwerth, B.; Feather, M.; Olesen, P. The precipitation and cross-linking of lens crystalline by ascorbic acid. Exp. Eye Res. 1988, 47, 155-168.
18. Patthy, L.; Smith, E. Reversible modification of arginine residues. J. Biol. Chem. 1975, 250, 557-564.
19. Pischetsrieder, M.; Larisch, B.; Müller, U.; Severin, T. Reaction of ascorbic acid with aliphatic amines. J. Agric. Food Chem. 1995, 43, 3004-3006.
20. Ranganna, S.; Setty, L. Nonenzymatic discoloration in dried cabbage, ascorbic acid-amino acid interactions. J. Agric. Food Chem. 1968, 16, 529-533.
21. 14 acid from sorbitol. J. Am. Chem. Soc. 1952, 74, 5161-5162.
22. 14C studies on browning of dehydroascorbic acid in an aqueous solution. J. Agric. Food Chem. 1991, 39, 1735-1737.
23. Shin, D.; Feather, M. 3-Deoxy-L-glycero-pentos-2-ulose (3-desoxy-L-xylosone) and L-threo-pentos-2-ulose (L-xylosone) as intermediates in the degradation of L-ascorbic acid. Carbohydr. Res. 1990, 208, 246-250.
24. Slight, S.; Feather, M.; Ortwerth, B. Glycation of lens proteins by the oxidation products of ascorbic acid. Biochim. Biophys. Acta 1990, 1038, 367-374.
25. Sopio, R.; Lederer, M. Reaction of 3-deoxypentosulose with N-methyl- and N,N-dimethylguanidine as model reagents for protein-bound arginine and for creatinine. Z. Lebensm. Unters. Forsch. 1995, 201, 381-386.
26. Takahashi, K. The reaction of phenylglyoxal with arginine residues in proteins. J. Biol. Chem. 1968, 243, 6171-6179.
27. Yamasaki, R.; Vega, A.; Feeny, R. Modification of available arginine residues in proteins by p-hydroxyphenylglyoxal. Anal. Biochem. 1980, 109, 32-40.