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Characterization of Leptazolines A–D, Polar Oxazolines from the Cyanobacterium Leptolyngbya sp., Reveals a Glitch with the “Willoughby–Hoye” Scripts for Calculating NMR Chemical Shifts

  • Jayanti Bhandari Neupane
    Jayanti Bhandari Neupane
    Department of Chemistry, University of Hawai‘i at Ma̅noa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States
  • Ram P. Neupane
    Ram P. Neupane
    Department of Chemistry, University of Hawai‘i at Ma̅noa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States
  • Yuheng Luo
    Yuheng Luo
    Department of Chemistry, University of Hawai‘i at Ma̅noa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States
    More by Yuheng Luo
  • Wesley Y. Yoshida
    Wesley Y. Yoshida
    Department of Chemistry, University of Hawai‘i at Ma̅noa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States
  • Rui Sun
    Rui Sun
    Department of Chemistry, University of Hawai‘i at Ma̅noa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States
    More by Rui Sun
  • Philip G. Williams*
    Philip G. Williams
    Department of Chemistry, University of Hawai‘i at Ma̅noa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States
    *E-mail: [email protected].
Cite this: Org. Lett. 2019, 21, 20, 8449-8453
Publication Date (Web):October 8, 2019
https://doi.org/10.1021/acs.orglett.9b03216
Copyright © 2019 American Chemical Society
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Supporting Info (3)»

Abstract

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The bioactivity-guided examination of a Leptolyngbya sp. led to the isolation of leptazolines A–D (14), from the culture media, along with two degradation products (5 and 6). Density functional theory nuclear magnetic resonance calculations established the relative configurations of 1 and 2 and revealed that the calculated shifts depended on the operating system when using the “Willoughby–Hoye” Python scripts to streamline the processing of the output files, a previously unrecognized flaw that could lead to incorrect conclusions.

Supporting Information

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b03216.

  • General experimental details, NMR spectra for 16, NMR calculation for 2, and picture of the producing organism (PDF)

  • Raw NMR data for all new compounds (ZIP)

  • Revised NMR-data_compilation Python scripts and instructions (ZIP)

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Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 2 publications.

  1. María M. Zanardi, Maribel O. Marcarino, Ariel M. Sarotti. Redefining the Impact of Boltzmann Analysis in the Stereochemical Assignment of Polar and Flexible Molecules by NMR Calculations. Organic Letters 2020, 22 (1) , 52-56. DOI: 10.1021/acs.orglett.9b03866.
  2. Patrick H. Willoughby, Matthew J. Jansma, Thomas R. Hoye. Addendum: A guide to small-molecule structure assignment through computation of (¹H and ¹³C) NMR chemical shifts. Nature Protocols 2020, 9 DOI: 10.1038/s41596-020-0293-9.

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