Structure assignment of lucentamycin e and revision of the olefin geometries of the marine-derived lucentamycins

Jin Wook Cha, Jin Soo Park, Taebo Sim, Sang Jip Nam, Hak Cheol Kwon, Juan R. Del Valle, William Fenical

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A new lucentamycin analogue, lucentamycin E (5), was isolated from the culture broth of the marine-derived actinomycete Nocardiopsis lucentensis, strain CNR-712. The absolute stereostructure of 5 was assigned by comprehensive analyses of NMR data and by application of the advanced Marfey's method. The planar structure of 5 was analogous to lucentamycins A-D, whereas the olefin geometry of the 3-methyl-4-ethylideneproline moiety was found to be E, opposite of that previously reported. Consequently, a reinvestigation of the olefin geometries of the 3-methyl-4-ethylideneproline residues of lucentamycins A-D showed that the olefin geometries of the substituted proline functionalities must be revised to (2S,3R,E)-3-methyl-4-ethylideneproline.

Original languageEnglish
Pages (from-to)1648-1651
Number of pages4
JournalJournal of Natural Products
Volume75
Issue number9
DOIs
Publication statusPublished - 2012 Sep 28

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Cha, J. W., Park, J. S., Sim, T., Nam, S. J., Kwon, H. C., Del Valle, J. R., & Fenical, W. (2012). Structure assignment of lucentamycin e and revision of the olefin geometries of the marine-derived lucentamycins. Journal of Natural Products, 75(9), 1648-1651. https://doi.org/10.1021/np3003854