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Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines

  • Ziran Li
    Ziran Li
    Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States
    More by Ziran Li
  • Zachary Gentry
    Zachary Gentry
    Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States
  • Brennan Murphy
    Brennan Murphy
    Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States
  • , and 
  • Michael S. VanNieuwenhze*
    Michael S. VanNieuwenhze
    Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States
    *E-mail: [email protected]
Cite this: Org. Lett. 2019, 21, 7, 2200–2203
Publication Date (Web):March 11, 2019
https://doi.org/10.1021/acs.orglett.9b00125
Copyright © 2019 American Chemical Society

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    Abstract

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    Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b00125.

    • Experimental procedures, spectroscopic data of the obtained compounds and copies of 1H and 13C NMR spectra (PDF)

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    Cited By

    This article is cited by 9 publications.

    1. Nuria Mazo, Imran R. Rahman, Claudio D. Navo, Jesús M. Peregrina, Jesús H. Busto, Wilfred A. van der Donk, Gonzalo Jiménez-Osés. Synthesis of Fluorescent Lanthipeptide Cytolysin S Analogues by Late-Stage Sulfamidate Ring Opening. Organic Letters 2023, 25 (9) , 1431-1435. https://doi.org/10.1021/acs.orglett.3c00122
    2. Laura Burchill, Luca Zudich, Phillip L. van der Peet, Jonathan M. White, Spencer J. Williams. Synthesis of the Alkylsulfonate Metabolites Cysteinolic Acid, 3-Amino-2-hydroxypropanesulfonate, and 2,3-Dihydroxypropanesulfonate. The Journal of Organic Chemistry 2022, 87 (6) , 4333-4342. https://doi.org/10.1021/acs.joc.2c00036
    3. Liang Tu, Zhenghui Li, Tao Feng, Shuyan Yu, Rong Huang, Jing Li, Wenxuan Wang, Yongsheng Zheng, Jikai Liu. Access to Imidazolidines via 1,3-Dipolar Cycloadditions of 1,3,5-Triazinanes with Aziridines. The Journal of Organic Chemistry 2019, 84 (17) , 11161-11169. https://doi.org/10.1021/acs.joc.9b01959
    4. Fengcai Zhang, Yu Zhang, Qingfa Tan, Lili Lin, Xiaohua Liu, Xiaoming Feng. Kinetic Resolution of Aziridines via Catalytic Asymmetric Ring-Opening Reaction with Mercaptobenzothiazoles. Organic Letters 2019, 21 (15) , 5928-5932. https://doi.org/10.1021/acs.orglett.9b02058
    5. Masaya Kumashiro, Kosuke Ohsawa, Takayuki Doi. Photocatalyzed Oxidative Decarboxylation Forming Aminovinylcysteine Containing Peptides. Catalysts 2022, 12 (12) , 1615. https://doi.org/10.3390/catal12121615
    6. Bolong Li, Arif Ali, Shutao Lei, Chen Zhao. Lipids to Fuels and Chemicals. 2022, 459-506. https://doi.org/10.1002/9783527815906.ch13
    7. Valentina Verdoliva, Giuseppe Digilio, Michele Saviano, Stefania De Luca. Microwave Heating Promotes the S-Alkylation of Aziridine Catalyzed by Molecular Sieves: A Post-Synthetic Approach to Lanthionine-Containing Peptides. Molecules 2021, 26 (20) , 6135. https://doi.org/10.3390/molecules26206135
    8. Jonathon S. Russel. Three-membered ring systems. 2021, 107-131. https://doi.org/10.1016/B978-0-323-89812-6.00003-1
    9. Adam G. Meyer, Alex C. Bissember, Christopher J.T. Hyland, Charlotte C. Williams, Monika Szabo, Steven M. Wales, Grace E.O. Constable, Wesley J. Olivier. Seven-membered rings. 2021, 565-614. https://doi.org/10.1016/B978-0-323-89812-6.00016-X

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