Arginine Maillard reaction

To study the effect of the Maillard reaction on nutritive value of protein, Patton, et a l. (57) heated purified casein and soybean globulin in 57. glucose solution for 24 hrs at 96.5°C, and found significant losses of lysine, arginine, tryptophan, and histidine (52). 

Conditions for the Synthesis of Antioxidative Arginine-Xylose Maillard Reaction Products... 

An antioxidative Maillard reaction product (AX) can be formed from arginine and xylose. Optimum results were obtained by refluxing 1M arginine-HCl with 1M xylose in water at 100°C for 10-20 h at initial pH of approximately 5. 

Foster, R. C. "Preliminary isolation and characterization of an antioxidative component of the Maillard reaction between arginine and xylose" M. S. Thesis, Oklahoma State University, Stillwater, Oklahoma, 1980 72 pp. 

Much attention has recently been paid to arginine as a melanoidin precursor. In a model system, lV -acetylarginine was first allowed to react with glyoxal in aqueous solution at pH 7, followed by furfural. Repeated chromatography of the aqueous residue after ethyl acetate extraction led to a 1% yield of the deep red 29.180 Such a compound provides an example of a potentially coloured crosslink in proteins derived by the Maillard reaction (see Chapter 8). 

T. Hofmann, 4-Alkylidene-2-imino-5-[4-alkylidene-5-oxo-l,3-imidazol-2-inyl]aza-methylidine-l,3-imidazolidine —A novel colored substructure in melanoidins formed by Maillard reactions of bound arginine with glyoxal and furan-2-carboxaldehyde, J. Agric. Food Chem., 1998, 46, 3896-3901. 

G. R. Waller, R. W. Beckel, and B. O. Adeleye, Conditions for the synthesis of antioxidative arginine-xylose Maillard reaction products, in B, 1983, 125-140. 

Beckel, R.W. and Waller, G.R. 1983. Antioxidative arginine-xylose Maillard reaction products conditions of synthesis. J. Food Sci. 48, 996—997. 

The new fluorescent pyrrolopyrimidinium compound 124 has been formed by Maillard reaction of 3-deoxyglucosone with n-butylamine, and likewise the novel imidazolone 125 from its reaction with lV-benzoyl-arginine. ° The synthesis of cyclic guanidinium derivatives incorporating 1,3-diamino-1,3-dideoxy-tetritol moieties as glycosidase inhibitors is detailed in Chapter 9, section 3.7. 

Cho, R.K, Okitani, A., and Kato, H. Polymerization of proteins and impairment of their arginine residues due to intermediate compounds in the Maillard reaction, in ""Amino-carbonyl reactions in food and biological systems. Development in Food Science. 13" Fujimaki, M., Namiki, M., Kato, H. Eds. Elsevier, Amusterdam, 1986, pp 439-448. 

More recently, non-sulfur fructosyl arginine, a Maillard reaction product, was isolated from AGE and was found to inhibit LDL oxidation (18), inhibit oxidized LDL-induced endothelial cell injury (18) and directly scavenging reactive oxygen species in cells and cell free systems (18, 19). 

Amino acid analysis confirmed that Maillard browning reactions occurred during the frying process, since basic amino acids such as lysine and arginine decreased significantly, whereas all others decreased only slightly (Table I). 

F. Gerum, M. O. Lederer, and T. Severin, Cross-linking of proteins by Maillard processes Model reaction of an Amadori compound with W -acctyl-l -arginine, in F. 1998, 409. 

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