Sugar amino acid reactions

T. E. Stewart, M Survey of the Chemistry of Amino Acids-Reducing Sugar Reaction in Relation to Aroma Production, Scientific and Technical Surveys No. 61, British Eood Manufacturing Industries Research Association, London, Dec. 1969. 

Ozone causes both quantitative and qualitative changes in carbon dioxide fixation patterns. Wilkinson and Bames, using carbon dioxide-found a reduction in radioactivity in soluble sugars and increases in free amino acids and sugar phosphates in white pine after a 10-min exposure to ozone at 0.10 ppm. Miller observed a decrease in carbon dioxide-fixation in ponderosa pines that correlated with loss of chlorophyll, after exposure to ozone at 0.30-0.35 ppm. The Hill reaction rates of chloroplasts isolated from healthy and ozone-injured ponderosa pine indicated that both light and dark reactions of the chloroplasts from ozone-injured plants were depressed. Barnes found depressed photosynthesis and stimulated respiration in seedlings of four pine species of the southeastern United States after exposure to ozone at 0.15 ppm. 

Some authors have indicated that the sugar-amino acid reactions of the Maillard type are of minor importance in citrus juices because of the high acidities involved. Studies in our laboratories (42-44) would tend to indicate that, to the contrary, the amino acids and sugars are of more than just minor importance in the darkening of citrus juices. Huffman (42) treated citrus juices with cationic ion-exchange resins to remove amino acids, proteins, and the mineral cations, then restored the cations. 

In 1911 his first report (3) on peptide synthesis was presented and in 1912 his first report (2 ) on the sugar-amino acid reaction was published. He completed a book (J l) in 1913. 

Because of their significant electrophilic character, aldehydes are often unstable and will react with nucleophiles. For example, a common reaction of aldehydes is the formation of a hemiaminal with amines. If the amine is a primary amine, the hemiaminal can dehydrate to form an imine as shown in Figure 21. The reaction of aldehydes with primary and secondary amines is a well-studied reaction pathway because it is a common reaction pathway of reducing sugars and amino acids, and this reaction pathway is known as the Maillard reaction (40). In the case of amino acids and sugars, this reaction leads to discoloration, or browning. This reaction will be discussed in greater detail in the Amines-Maillard Reaction section. 

Absence of catalysis Condensation reaction between basic amino acids and sugars in the absence of catalysts results in N-rich polymers similar to humic substances in marine environments Hedges (1978)... 

Useful for such compounds as sugars, phenols, alcohols, amines, thiols, steroids especially recommended for citric acid cycle compounds and amino acids reaction is often carried out in pyridine or dimethyl formamide (the latter being preferred for 17-keto steroids) care must be taken to eliminate moisture lowest silyl donating strength of all common silating reagents... 

As a result of the very wide chemical interest which the Maillard reaction has attracted since the early years of this century, and of its diverse commercial and biological implications, a vast amount of work thereon has been published. In this article, the chemical aspects of the reaction between simple amino acids and mono- and di-saccharides will be surveyed the reaction with peptides and proteins will be discussed only when it contributes to our understanding of the mode of interaction between simple amino acids and sugars. The significance of the reaction in the preservation of various foodstuffs has now been reviewed many times2 9 and continues to be the subject of much investigation.10 16 The reaction is also... 

Many other compounds have been identified as products of the sugar-amino acid reaction. Amongst these are 2,3-butanedione,195 formaldehyde,196 pyruvaldehyde,20,195, 247, 248 3-hydroxy-2-butanone,248 hydroxy-2-propanone,248 and acetaldehyde.73 Imidazoles,196, 249-251 especially 4(5)-methylimidazole, have also been isolated from the reaction under mild conditions, and could have been formed from a-hydroxy ketones or aldehydes plus amino compounds. Following the early identification247 of pyru-valdehyde as a product of the Maillard reaction, much work was done in an attempt to show that this reactive compound plays a major role in the reaction,249 262 254 but, that this is so is by no means certain.7... 

A common thread that can link the ammonium and peptone catalyst poisoning results just described could be the Maillard reactions of amino acids with sugars (5). Recent studies have shown that the ammonium ion is highly reactive, more so than substituted versions (6). Its use as ammonium bicarbonate in developing flavoring compounds by Maillard reactions in extrusion cookers has been reported (7). It is likely that such reactions could occur at our processing conditions. We can speculate that such products could have acted as catalyst surface poisons, which might have been subsequently washed from the catalyst, before it was reused in its active form. 

The aroma precursors have been selected by taking into account the significant role of the Maillard reaction. Indeed, most aroma compounds of this type are formed by the reaction of amino acids with sugars or their degradation products. So we have obtained roast beef, roast mutton and heated vegetable aromas after having treated a mixture of amino acids and glucose at different temperatures and for varied times. 

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