Metal-Binding Ability of Leu-Enkephalin, Related Glycoconjugates and Peptidomimetics

Both the chemistry and consequences of the nonenzymatic reaction between reducing sugars and reactive amino groups of amino acids, peptides and proteins (known as the Maillard reaction), have received considerable attention in food and health science fields. This initial reaction results in Amadori and similar products formation, followed by degradation to advanced glycation end products (AGEs). It is well established that AGEs are associated with color and odor of thermally processed or stored food, as well as with pathogen products in a number of diseases. The model systems of early stage Maillard reaction products (MRP) were prepared between endogenous opioid peptide leucine enkephalin (1) and D-glucose/D-glucuronic acid. The complexation ability of prepared MRP with metal ions (Ca2+, Zn2+, Al3+, Pb2+ and Cu2+) was investigated and compared to the complexation ability of parent peptide using ECD and FTIR spectroscopic measurements.