Abstract
Peptidomimetics that can coordinate transition metals have a variety of potential applications as catalysts, sensors, or materials. A new modular peptidomimetic scaffold, the “azole peptoid”, is introduced here. We report methods for the solid-phase synthesis of eleven examples of trimeric N-substituted oligoamides that include oxazole- or thiazole-functionalized backbones. The products prepared comprise a diversity of functionality, including a metal-coordinating terpyridine group. The modular synthetic approach enables ready preparation of analogs for specific applications. To highlight a potential use of this new synthetic scaffold, a trimeric azole peptoid functionalized with a terpyridine residue was prepared and studied. The characteristic 2:1 ligand:metal binding of this terpyridine-functionalized azole peptoid to Zn2+ in aqueous solution was observed. These studies introduce azole peptoids as a useful class of biomimetic molecules for further study and application.
Highlights
IntroductionOne function of natural biopolymers that researchers have sought to recapitulate with modular, bio-inspired oligoamide scaffolds is the ability to coordinate transition metals in aqueous solution
One function of natural biopolymers that researchers have sought to recapitulate with modular, bio-inspired oligoamide scaffolds is the ability to coordinate transition metals in aqueous solution.Metal-binding peptidomimetics have potential application as sensors [1,2] or catalysts [3,4], for example.Naturally-occurring molecules, including peptides and peptide-derived natural products, frequently feature well-defined three-dimensional structures that display ligands in a specific arrangement to coordinate to metals
The methods developed in this work conserve azole reagent 1, which must be synthesized
Summary
One function of natural biopolymers that researchers have sought to recapitulate with modular, bio-inspired oligoamide scaffolds is the ability to coordinate transition metals in aqueous solution. Naturally-occurring molecules, including peptides and peptide-derived natural products, frequently feature well-defined three-dimensional structures that display ligands in a specific arrangement to coordinate to metals. Synthetic oligoamides (i.e., peptidomimetics) offer similar capabilities to display functionality in a spatially controlled manner [5,6,7,8]. Non-natural peptidomimetics have the added advantage that well-studied metal-coordinating ligands not found in biomolecules (e.g., phenanthroline, bipyridine, hydroxyquinoline, or terpyridine) can be appended [9,10]. Azole metal-coordinating groups are commonly found in peptide-derived natural products [11]
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