Maillard reaction compounds formed

Maillard reaction products formed by interaction of reducing sugar and amino acids such as a-dicarbonyl compounds, aldehydes, hydrogen sulfide, and ammonia can react further to form derivatives that have been identified from meat or its components during heating. Important reviews of sulfur compounds that might be produced by these reactions have been published by Schutte (35) and... 

Hydrolyzed vegetable protein (HVP) is one of the earliest known forms of thermal reaction or process flavors (7,2). HVPs can been produced by acid (HCl) or enzyme (proteolytic) hydrolysis of a protein source (usually of plant origin) to form principally amino acids (7,5-5), which, themselves, can impart taste (e.g. monosodium glutamate) or participate in subsequent thermal reactions, e.g. Maillard reaction, to form aroma compounds (6,7). Among the numerous process parameters involved in the production of HVP, the substrate or protein source material may have a great in5)act on the resulting amino acid profile and flavor characteristics of the final product (7,5). 

Other possible mechanisms for the formation of pyrazines during smoking are possible. For instance, leaf carbohydrates could be degraded either through pyrolysis or Maillard reactions to form a-dicarbonyl compounds, which could, in turn, react with amino acids to undergo a Strecker degradation forming... 

In our investigation on the effect of Maillard reaction products on the absorption of tryptophan (36), the kinetics of the absorption of tryptophan in the presence of Maillard reaction products formed in the glucose-tryptophan system was studied by bott vitro everted gut sac method and vivo catherization of the portal vein. Fructose-L-tryptophan (Amadori compound) appeared to be the major fraction of the reaction products when fractionated using a cellulose column eluted by water-saturated n-butanol. The absorption of L-tryptophan was partially inhibited vitro and vivo by fructose-L-tryptophan in a competitive manner with an inhibitor constant (Ki) of l.lmM. The relative absorption rate of L-tryptophan was significantly lower in the presence of the Maillard reaction products than in the presence of fructose-L-tryptophan indicating the presence of other inhibitory factors in the reaction products. The in vivo absorption of fructose-L-tryptophan was almost negligible compared to that of tryptophan. The inhibited absorption by Maillard reaction products, may have contributed in part to an incomplete recovery in the growth of the rats when fed a supplemented browned synthetic amino acid diet. 

Maillard reaction. We are sure, however, they do not represent artefacts, formed upon work up or during the analytical procedure. Several of the heterocycles have been described earlier as volatile constituents of mother s milk (Pellizari et al. 1982 cf. Figure 31.2 compounds 5, 6, 9, 13, 17, 19 among other unknown oxygen con-... 

Electron-spin resonance (e.s.r.) spectra with characteristic hyperfine structure have been recorded during the initial stages of the Maillard reaction between various sugar and amino compounds. The products responsible for the spectra appear to be IV, Af -disubstituted pyrazine radical cations. The pyrazine derivatives are assumed to be formed by the bimolecular condensation of two- and three-carbon enaminol compo-... 

The Maillard reaction is inextricably linked to the desirable flavour and colour characteristics of cooked foods and this review provides an insight into some of the chemistry associated with flavour generation in the reaction and the different aromas which are involved. The chemical pathways associated with the initial and intermediate stages of the Maillard reaction are presented and routes by which the important classes of aroma compounds may be formed from Maillard intermediates are discussed. 

Classes of Aroma Compounds Formed in the Maillard Reaction... 

Hydrogen sulphide is a key intermediate in the formation of many heterocyclic sulphur compounds. It is produced from cysteine by hydrolysis or by Strecker degradation ammonia, acetaldehyde and mercaptoacetaldehyde are also formed (Scheme 12.4). All of these are reactive compounds, providing an important source of reactants for a wide range of flavour compounds. Scheme 12.6 summarises the reactions between hydrogen sulphide and other simple intermediates formed in other parts of the Maillard reaction. 

The reaction of dextrose with a nitrogen-containing compound, eg, amino acids or proteins, yields a series of intermediates which form pigments of varied molecular weight (Maillard reaction). The type of pigments produced is dependent on reaction conditions such as pH, temperature, and concentration of reactants. 

Formation of novel free radical products at an early stage of the Maillard reaction was demonstrated by use of ESR spectrometry. Analyses of the hyperfine structures for various sugar-amino compound systems led to the conclusion that the radical products are N,N -disubstituted pyrazine cation radicals. These new pyrazine derivatives are assumed to be formed by bimolecular condensation of a two-carbon enaminol compound involving the amino reactant residue. The presence of such a two-carbon product in an early stage reaction mixture of sugar with amine was demonstrated by isolation and identification of glyoxal dialkylimine by use of TLC, GLC, NMR, MS and IR. 

Many desirable meat flavor volatiles are synthesized by heating water-soluble precursors such as amino acids and carbohydrates. These latter constituents interact to form intermediates which are converted to meat flavor compounds by oxidation, decarboxylation, condensation and cyclization. 0-, N-, and S-heterocyclics including furans, furanones, pyrazines, thiophenes, thiazoles, thiazolines and cyclic polysulfides contribute significantly to the overall desirable aroma impression of meat. The Maillard reaction, including formation of Strecker aldehydes, hydrogen sulfide and ammonia, is important in the mechanism of formation of these compounds. 

Several mechanisms have been reported for pyrazine formation by Maillard reactions (21,52,53). The carbon skeletons of pyrazines come from a-dicarbonyl (Strecker) compounds which can react with ammonia to produce ot-amino ketones as described by Flament, et al. (54) which condense by dehydration and oxidize to pyrazines (Figure 6), or the dicarbonyl compounds can initiate Strecker degradation of amino acids to form ot-amino ketones which are hydrolyzed to carbonyl amines, condensed and are oxidized to substituted... 

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