Biomimetic Utilization of Metal-Binding Peptoids for Cooperative Catalysis and Recognition

Galia Maayan, Schulich Faculty of Science, Technion, Haifa, Israel

N-substituted glycine oligomers, “peptoids”, are a class of peptidomimetics that are generated from primary amines rather than from amino acids. Thus, their facile and efficient synthesis on solid phase support enables the incorporation of various functional groups at specified N-positions along their spine. Capitalizing on this property, we design and produce peptoid sequences having metal-binding ligands displayed in a specific manner, and investigate whether their interaction with biologically relevant metal ions can induce biomimetic function. We demonstrate that: (1) catalytic Cu(I)-TEMPO peptoids can perform with much higher activity in the oxidation of alcohols than a mixture of Cu(I) and TEMPO and (2) peptoids incorporating two different ligands enable both the selective binding of two different metal ions, one at each site, as well as the selective binding of Cu(II) from a mixture of numerous metal ions in higher concentrations.