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Molecules 2018, 23(6), 1475; https://doi.org/10.3390/molecules23061475

Recent Reports of Solid-Phase Cyclohexapeptide Synthesis and Applications

Department of Pharmaceutical Sciences, The Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, 34 Rainbow Drive, Hilo, Hawaii, HI 96720, USA
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Academic Editor: Viktor Krchnak
Received: 16 May 2018 / Revised: 11 June 2018 / Accepted: 16 June 2018 / Published: 18 June 2018
(This article belongs to the Special Issue Solid Phase Synthesis)
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Abstract

Macrocyclic peptides are privileged scaffolds for drug development and constitute a significant portion of macrocyclic drugs on the market today in fields spanning from infectious disease to oncology. Developing orally bioavailable peptide-based drugs remains a challenging task; however, macrocyclization of linear peptides can be an effective strategy to improve membrane permeability, proteolytic stability, oral bioavailability, and overall drug-like characteristics for this class. Significant advances in solid-phase peptide synthesis (SPPS) have enabled the efficient construction of macrocyclic peptide and peptidomimetic libraries with macrolactamization being performed on-resin or in solution phase. The primary goal of this review is to summarize solid-phase cyclohexapeptide synthesis using the on-resin and solution-phase macrocyclization methodologies published since 2013. We also highlight their broad applications ranging from natural product total synthesis, synthetic methodology development, and medicinal chemistry, to drug development and analyses of conformational and physiochemical properties. View Full-Text
Keywords: cyclohexapeptide; solid-phase synthesis; total synthesis; macrocyclization; macrolactamization; structure–activity relationship; natural products; on-resin cyclization; solution-phase cyclization cyclohexapeptide; solid-phase synthesis; total synthesis; macrocyclization; macrolactamization; structure–activity relationship; natural products; on-resin cyclization; solution-phase cyclization
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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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Prior, A.M.; Hori, T.; Fishman, A.; Sun, D. Recent Reports of Solid-Phase Cyclohexapeptide Synthesis and Applications. Molecules 2018, 23, 1475.

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