Czech J. Food Sci., 2004, 22(10):S93-S95 | DOI: 10.17221/10624-CJFS
A new pathway of lactose degradation and arginine derivatization in milk
- Institute of Food Chemistry, Technical University Dresden, Dresden, Germany, *E-mail: elvira.mavric@chemie.tu-dresden.de
Abstract: Recently, N-δ-[5-(3-hydroxypropyl)-4-oxo-imidazolon-2-yl]--ornithine (PIO) was identified as a new arginine derivative, formed exclusively from the side-chain of peptide-bound arginine and degradation products of oligosaccharides with 1,4-glycosidic linkages, thus probably representing the major form of arginine derivatization in heated milk products. The formation mechanism of PIO was clarified via identification of a previously unknown C5 dicarbonyl precursor, namely 3,4-dideoxypentosulose (3,4-DDPs). 3,4-DDPs was isolated as the corresponding chinoxaline from reaction mixtures containing N-α-hippuryl arginine, lactose and o-phenylendiamine using semipreparative RP-HPLC. Identification was achieved using LC-MS as well as 1H- and 13C-NMR. The formation of 3,4-DDPs from lactose follows a new pathway of carbohydrate degradation in foods.
Keywords: arginine derivatization; lactose; 3,4-dideoxypentosulose; Maillard reaction
Published: December 31, 2004 Show citation
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