Compounds from reaction with cysteine

Cysteine is an important precursor of meat flavor and is therefore often being used in precursor systems for the industrial production of meat process flavorings (1-4). Meat flavor development in these systems is usually based on the Maillard reaction of cysteine (and other amino acids) with sugars. Unfortunately, there are a few complications that prevent that high yields of volatile flavor compounds are obtained from these reactions. The first... 

Silverman and Zieske have rationalized how a protein nucleophile other than flavin is involved in MAO inactivation reactions, and why different inactivator compounds specifically react with flavin, protein amino acids, or both (100). Hydrogen atom donation from a cysteine residue to the flavin semiquinone radical would produce a thiyl radical, which could then capture the primary or secondary alkyl radical generated on cyclopropyl ring opening from the amine radical cation of the inactivator. The hydrogen atom abstraction reaction between the flavin and active site amino acid may be an equilibrium process such that either species could be present at any turnover. Hence, a combination of steric constraints and proximity to either the flavin semiquinone radical or the thiol radical will determine the site of adduct formation for a particular inactivator structure. A two-dimensional representation is shown in Scheme 23 (compounds 40-42), which illustrates the proposed equilibrium between the flavin semiquinone radical and amino acid as well as the proposed intermediates for the inactivation of MAO by A-(l-methylcyclopropyl)benzylamine 40 (104), rrradical center relative to the particular protein radical is consistent with proposed site of attachment of inactivator to protein 40 is near the flavin radical, such that exclusive flavin attachment occurs, 41 is positioned closer to the amino... 

Zhang Y. and Ho C.T. (1991) Comparison of the volatile compounds formed from the thermal reaction of glucose with cysteine and glutathione. J. Agric. Food Chem. 39, 760-3. 

R. Bogndr, L. Somogyi, and Z. Gyorgydeak, Heterocyclic compounds from sugars. III. Substituted thiazohdines by reactions of L-cysteine with monosaccharides, Justus Liebigs Ann. Chem., 738 (1970) 68-78. 

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