Quantification of Chemically Reducing Species in the Phosphate Ion Catalyzed Degradation of Reducing Sugars

Abstract

Chemically reducing species formed during phosphate ion catalyzed degradation of reducing sugars were directly quantified by titration with 2,6-dichloroindophenol (Tillman's reagent) and by measurement of open circuit electrical redox potentials. Both techniques demonstrated a time-dependent increased production of chemically reducing species in 0.1 M phosphate buffer at 100 degrees C and the increasingly negative redox potentials observed were consistent with the formation of reductones. Cyclic voltammetry (CV) was investigated in an attempt to generate and observe the sugar-derived highly reactive reducing species in situ. CV analysis of a model Amadori compound, N-(1-deoxyfructos-1-yl)piperidine, indicated oxidative waves consistent with reductone formation, but chemical instability of the oxidation products formed precluded the electrochemical detection of highly electrophilic reducing species such as reductones.

Effect of the C-Ring Structure of Flavonoids on the Yield of Adducts Formed by the Linkage of the Active Site at the A-Ring and Amadori Rearrangement Products during the Maillard Intermediate Preparation

“…Conversely, when DM, EC, PG, DQ, and EGC were added to the samples reacting for 80 min in the first low-temperature step, the Thr-ARP that had accumulated in large quantity would react with the added DM, EC, PG, DQ, or EGC to generate the DM-Thr-ARP, EC-Thr-ARP, PG-Thr-ARP, DQ-Thr-ARP, or EGC-Thr-ARP. In this way, the degradation of Thr-ARP was inhibited, and the production of α-dicarbonyl compounds was decreased (Figure S11); the α-dicarbonyl compounds were proved to be the key intermediates for the formation of melanoidins, and they would participate in the formation of the melanoidin skeleton. , Thus, the production of melanoidins was partially blocked because of the lack of core precursor substances (α-dicarbonyl compounds), which caused an A 420 decrease in the samples reacting for 80 min in the first low-temperature step (Figure a).…”

Formation and migration of α‐dicarbonyl compounds during storage and reheating of a sugary food simulation system

“…Rearrangement, reduction, dehydration, and hydrolysis of 1‐DG could also result in 2,3‐BD formation. MGO is formed by retroaldolization of 3‐DG …”

“…The formation of MGO from glucose proceeds by 2,3‐enolization, retro‐aldol condensation, and deglyceraldehyde. The glucose was degraded generating GO by retro‐aldol condensation …”

“…MGO is formed by retroaldolization of 3-DG. 22,23 In addition to MRs, ⊍-DCs could also be formed by fragmentation of the sugar moiety during retro-aldol condensation and auto-oxidation in the absence of proteins and amino acids. For example, 3-DG is formed by 2,3-enolization and dehydration of glucose.…”

“…The glucose was degraded generating GO by retro-aldol condensation. 12,22 During storage, the concentration of ⊍-DCs declined, that may because of their volatility or reactions with other compounds. The sugar content did not decrease significantly during storage for 20 days (Fig.…”