FOOD 2400 Lecture Notes - Lecture 1: Amadori Rearrangement, Maillard Reaction, Glycosylamine

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Carbohydrate-protein interactions are reactions that cause deterioration of food and the loss of its nutritional quantity [1]. These reactions are often between amines, amino acids, peptides or proteins and either sugars and vitamin c; known as nonenzymatic browning or maillard reaction, or quinones; known as enzymatic browning [1]. During the maillard reaction, the carbonyl group on the reducing sugar is in a linear form, which allows the reducing sugar to react with a non-ionized amino compound [2]. Water is then lost, and a ring structure is formed called a glycosylamine [2]. This compound undergoes the amadori rearrangement, producing 1-amino-2-keto sugar, which then degrades by 3-deoxyhexosone or methyl-dicarbonyl [2]. On the other hand, if the reducing sugar is a ketose, then the glycosylamine compound undergoes the heyns rearrangement forming a 2- amino aldose [2]. Nevertheless, enzymatic browning is initiated by the combination of the enzyme phenolase and phenolic substrate when the surface of the fruit or vegetable is cut.

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