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Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea

  1. Author:
    Yan, Pengcheng [ORCID]
    Li, Ge
    Wang, Chaojie
    Wu, Jianzhang
    Sun, Zhongmin
    Martin, Gary E
    Wang, Xiao [ORCID]
    Reibarkh, Mikhail
    Saurí, Josep
    Gustafson,Kirk [ORCID]

  2. Author Address

    School of Pharmaceutical Sciences , Wenzhou Medical University , Wenzhou , Zhejiang 325035 , People 39;s Republic of China., Institute of Oceanology , Chinese Academy of Sciences , Qingdao 266071 , People 39;s Republic of China., Department of Chemistry and Biochemistry , Seton Hall University , South Orange , New Jersey 07079 , United States., Structure Elucidation Group, Analytical Research and Development , Merck & Co. , Rahway , New Jersey 07065 , United States., Structure Elucidation Group, Analytical Research and Development , Merck & Co. , Boston , Massachusetts 02115 , United States., Molecular Targets Program, Center for Cancer Research , National Cancer Institute , Frederick , Maryland 21702 , United States.,
    1. Year: 2019
    2. Date: Sep 20
    3. Epub Date: 2019 09 06
  2. Journal: Organic letters
    1. 21
    2. 18
    3. Pages: 7577-7581
  4. Type of Article: Article
  5. ISSN: 1523-7060
  1. Abstract:

    The challenging structural motif of dictyospiromide (1), a spirosuccinimide alkaloid with antioxidant properties that are associated with activation of the Nrf2/ARE signaling pathway, was assigned using contemporary NMR experiments complemented with anisotropic NMR, chiroptical, and computational methodologies. Anisotropic NMR parameters provided critical orthogonal verification of the configuration of the difficult to assign spiro carbon and the other stereogenic centers in 160;1.

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  1. Keywords:

External Sources

  1. View Full Text
  2. DOI: 10.1021/acs.orglett.9b02856
  3. PMID: 31539931
  4. View record in Web of Science®
  5. WOS: 000487577200081

Library Notes

  1. Fiscal Year: FY2019-2020
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