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Rational Design and Synthesis of Post-Functionalizable Peptide Foldamers as Helical Templates

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Division of Organic Chemistry and Division of Pharmacology, National Institute of Health Sciences, Tokyo 158-8501, Japan
Cite this: Bioconjugate Chem. 2017, 28, 12, 3029–3035
Publication Date (Web):November 14, 2017
https://doi.org/10.1021/acs.bioconjchem.7b00621
Copyright © 2017 American Chemical Society

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    Abstract

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    In this study, we developed post-functionalizable helical peptides composed of Leu, Aib, and Azl residues. We show that the synthesized peptides 1 and 2 form helical structures, and may be modified using specific side chain or several functional groups by the click reaction without influencing their secondary structures.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.bioconjchem.7b00621.

    • Information about the synthetic scheme and copies of the 1H NMR and 13C NMR spectra of compounds 1, 2, 5, 8, 9, and 12, and HPLC data of peptides FAM-1, FAM-2, FAM-14, FAM-15, FAM-16, and FAM-17 (PDF)

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    Cited By

    This article is cited by 7 publications.

    1. Sherrie L. Heinz-Kunert, Ashma Pandya, Viet Thuc Dang, Julia Oktawiec, Andy I. Nguyen. Pore Restructuring of Peptide Frameworks by Mutations at Distal Packing Residues. Biomacromolecules 2024, 25 (3) , 2016-2023. https://doi.org/10.1021/acs.biomac.3c01418
    2. Genichiro Tsuji, Takashi Misawa, Mitsunobu Doi, Yosuke Demizu. Extent of Helical Induction Caused by Introducing α-Aminoisobutyric Acid into an Oligovaline Sequence. ACS Omega 2018, 3 (6) , 6395-6399. https://doi.org/10.1021/acsomega.8b01030
    3. Cristina Piras, Monica Pibiri, Stella Conte, Gabriella Ferranti, Vera Piera Leoni, Sonia Liggi, Martina Spada, Sandro Muntoni, Pierluigi Caboni, Luigi Atzori. Metabolomics analysis of plasma samples of patients with fibromyalgia and electromagnetic sensitivity using GC–MS technique. Scientific Reports 2022, 12 (1) https://doi.org/10.1038/s41598-022-25588-2
    4. Takashi Misawa. Fundamental Studies on Development of Next-generation Medium Sized Peptide Drugs. YAKUGAKU ZASSHI 2022, 142 (10) , 1061-1066. https://doi.org/10.1248/yakushi.22-00115
    5. Hidetomo Yokoo, Takashi Misawa, Takuma Kato, Masakazu Tanaka, Yosuke Demizu, Makoto Oba. Development of delivery carriers for plasmid DNA by conjugation of a helical template to oligoarginine. Bioorganic & Medicinal Chemistry 2022, 72 , 116997. https://doi.org/10.1016/j.bmc.2022.116997
    6. Hidetomo Yokoo, Motoharu Hirano, Takashi Misawa, Yosuke Demizu. Helical Antimicrobial Peptide Foldamers Containing Non‐proteinogenic Amino Acids. ChemMedChem 2021, 16 (8) , 1226-1233. https://doi.org/10.1002/cmdc.202000940
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