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Molecules 2018, 23(5), 1035; https://doi.org/10.3390/molecules23051035

Solid-Phase Synthesis of Azole-Comprising Peptidomimetics and Coordination of a Designed Analog to Zn2+

Department of Chemistry & Biochemistry, Santa Clara University, Santa Clara, CA 95053, USA
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Author to whom correspondence should be addressed.
Academic Editor: Viktor Krchnak
Received: 6 April 2018 / Revised: 23 April 2018 / Accepted: 26 April 2018 / Published: 28 April 2018
(This article belongs to the Special Issue Solid Phase Synthesis)
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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. View Full-Text
Keywords: peptidomimetic; oligoamide; heterocycle; metal coordination peptidomimetic; oligoamide; heterocycle; metal coordination
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Mohan, A.; Koh, A.H.M.; Gate, G.; Calkins, A.L.; McComas, K.N.; Fuller, A.A. Solid-Phase Synthesis of Azole-Comprising Peptidomimetics and Coordination of a Designed Analog to Zn2+. Molecules 2018, 23, 1035.

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