[Structural and equilibrium studies of the proton and copper(II) complexes of N-D-gluconylglycine]

N-D-Gluconylglycine, a pseudopeptide derivative glucono-delta-lactone and glycine, was prepared and the equilibrium constants of its protonation and copper(II) coordination and the structures of the copper complexes formed were studied in aqueous solution by potentiometry, spectrophotometry, CD, EPR and 13C-NMR relaxation. The parent complexes formed in acidic medium have low stabilities, characteristic of carboxylate coordination. In the pH range 5-9, the amide group and the 2-OH group of the ligand undergo deprotonation. In parallel with these processes, one ligand is replaced from the copper(II) coordination sphere. For the species MLH-2' we propose (30, 1N) coordination in the equatorial plane around the copper(II). EPR measurements indicate that dimeric species are also formed. At pH > 9, further base-consuming processes start as an indication of the deprotonation of other alcoholic hydroxy groups of the sugar moiety or the formation of mixed hydroxy complexes.