Novel Insights into the Maillard Catalyzed Degradation of Maltose

Abstract

Numerous investigations concerning Maillard degradation of carbohydrates clearly depict the important impact of α-dicarbonyl compounds on changes occurring during preparation of food or physiological processes in vivo. To study the formation of these reactive intermediates during degradation of maltose in the presence of lysine, α-dicarbonyl compounds were isolated, identified and quantified after reaction with o-phenylenediamine to form their stable quinoxaline derivatives. Maltosone and 1,4-dideoxyglucosone were synthesized and incubated independently with lysine to investigate follow-up products and to gain further insights into the complex degradation mechanisms. Glyoxylic acid as a dicarbonyl structure and 5,6-dihydroxy-2,3-dioxohexanal as a 1,2,3-tricarbonyl compound were established as novel Maillard degradation products of maltose. Conducted experiments unequivocally demonstrated that inter- and intramolecular redox reactions are of major importance during degradation of disaccharides. 1,4-Dideoxyglucosone, 1-lysino-1,4-dideoxyglucosone, 5,6-dihydroxy-2,3-dioxohexanal, 3,4-dideoxypentosone and glyoxylic acid were found to be the central intermediates involved in the redox chemistry. With the present study we deliver a comprehensive overview on the mechanisms behind α-dicarbonyl compounds evolving from Maillard degradation of maltose.

Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

“…Consequently, there must be alternative precursors for oxalic acid-Q formation to oxalic acid itself. 3,4-DDP is a known intermediate of maltose degradation but was found in neither the glucose nor ASA reaction systems (38). Hence, the origin of the detected 3,4-DDP-Q remains unknown.…”

“…In Maillard chemistry, glyoxylic acid is assigned to disaccharide chemistry (38) but can also arise from oxidation of glyoxal (68) and degradation of DHA (65,69). However, this cannot account solely for the plasma levels, which were 2.5-fold higher than GO and in the same range as 2,3-DKG.…”

“…The quinoxaline derivatives of the ␣-DCs will be marked hereafter with the suffix "-Q". 1-DG-Q, 3-DG-Q, glucosone-Q, Lederer's glucosone-Q, 1-DP-Q, 3-DP-Q, 3,4-DDP-Q, pentosone-Q, 1-DT-Q, 3-DT-Q, threosone-Q, pyruvic acid-Q, glyoxylic acid-Q, oxalic acid-Q, and 3-DG were synthesized according to our previous work (37)(38)(39). The identities of target compounds were verified by nuclear magnetic resonance (NMR) experiments.…”

Effect of Maillard reaction on reducing power of malts and beers

“…Thus, the level of DDMP may be substantially affected by the degree of beer ageing and redox status. Smuda and Glomb (2011) depicted the importance of the redox processes during Maillard degradation of maltose. They suggest 1-amino acid-1,4-dideoxyglucosulose as a highly potent player to undergo intermolecular redox reactions.…”

Engineering of Escherichia coli to facilitate efficient utilization of isomaltose and panose in industrial glucose feedstock

“…However, saccharides that contain α-1,6 bonds, such as isomaltose and panose, are not used up during E. coli fermentation because E. coli cannot assimilate isomaltose and panose as carbon sources. Furthermore, these sugars, which contain reducing sugar moieties, can react with free amino groups of amino acids during the purification step (Smuda and Glomb 2011;Ledl and Schleicher 1990); this so-called Maillard reaction decreases the yield of the final product and contaminates the reaction mixture with undesirable compounds. These problems must be overcome in order to increase the yield and productivity of fermentation when using glucose feedstock as a carbon source.…”