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Open AccessArticle

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
Author to whom correspondence should be addressed.
Academic Editor: Viktor Krchnak
Molecules 2018, 23(5), 1035;
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)
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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MDPI and ACS Style

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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