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 journalArticlepeer-review

13 Scopus citations

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
StatePublished - 28 Sep 2012

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