Sugar-Conjugated Bis(glycinato)copper(II) Complexes and Their Modulating Influence on the Maillard Reaction.

Abstract

Transition metal ions are known to play an important role in the Maillard reaction in catalyzing redox reactions. They can also form strong binary complexes with amino acids with increased reactivity toward smaller aldehydes. To take advantage of this enhanced reactivity and to demonstrate the ability of glucose to conjugate with glycine copper complexes, model systems containing (Gly)2Cu and glucose or their isotopically enriched counterparts were heated in aqueous solutions in the presence and absence of paraformaldehyde at 110 °C for 2 h and the residues were analyzed by electrospray ionization/quadrupole time-of-flight/mass spectrometry (ESI/qTOF/MS). Isotope-labeling studies have indicated the ability of (Gly)2Cu complexes to act as molecular scaffolds and undergo multiple reactions with glucose to generate various complexes of sugar conjugates. These relatively stable intermediates allowed for the slower release of aroma and browning precursors, such as Amadori products, during heating, as assessed by the extent of browning and total volatile release.