Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including N^α-Acetyllysine

Abstract

The reaction of l-dehydroascorbic acid (DHA) with primary aliphatic amines including N α-acetyllysine was examined by HPLC. A new aminoreductone, 2-deoxy-2-(propylamino)ascorbic acid (1) was isolated and the structure elucidated by spectroscopic data. Furthermore oxalic acid mono- (2) and diamides (3) were identified as important degradation products of DHA under Maillard conditions. 3-Deoxy-3-(alkylamino)ascorbic acids (4), typical condensation products of l-ascorbic acid and amines, were also detected in the reaction mixtures of DHA. All products are formed under oxidative and nonoxidative conditions from DHA. Keywords: Maillard reaction; l-dehydroascorbic acid; l-ascorbic acid; oxalic acid amides; aminoreductones; protein glycation; protein cross link

Determination of theMaillard product oxalic acidmonolysinylamide (OMA) in heated milk products by ELISA

“…In early experiments, OMA was identified as a Maillard product which was formed from L-ascorbic acid [20]. When proteins had been incubated with different sugars, significant binding of the anti-OMA antibody was only detected when dehydroascorbic acid or D-ribose were used as precursor [21].…”

L-Ascorbic Acid: Properties and Ways of Modification (A Review)

“…Since DAA always accompanies AsA under physiological conditions, it was suggested [71] that DAA rather than AsA interacts with amino groups. In most works devoted to the interactions of AsA with amino acids and proteins, only the products of these reactions were studied, while the mechanisms (including the possible formation of DAA in the intermediate stages) were given much less attention.…”

“…Essentially the same products where isolated when the reactions were conducted in THF at 40°C. Such reactions can also proceed under mild, nearly physiological conditions [71]. The general scheme of these processes can be subdivided into several directions [71].…”

“…Such reactions can also proceed under mild, nearly physiological conditions [71]. The general scheme of these processes can be subdivided into several directions [71]. The first stage involves the formation of Schiff bases 78 or 79 with primary amines at the 2-or 3-cerbonyl group of DAA (scheme 27).…”

Dehydroascorbic Acid Adducts of Guanosine Residues: Possible Biological Implications

“…[16,17] However, little is known about the reaction of DHA with amino acids, or proteins, although it is proposed that such interactions are responsible for browning pigments. [18][19][20] Recent studies suggest that some properties of AA and DHA involve either free-radical formation or inhibition of certain kinase activities. [21,22] Although, the adducts of certain 1,2-dicarbonyl compounds with guanines are known, [23] the binding of DHA with guanosine has never been reported.…”