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Insights into Lomaiviticin Biosynthesis. Isolation and Structure Elucidation of (−)-Homoseongomycin

Author:
Woo, Christina M., Gholap, Shivajirao L., Herzon, Seth B.
Source:
Journal of natural products 2013 v.76 no.7 pp. 1238-1241
ISSN:
1520-6025
Subject:
bacteria, biosynthesis, culture media, fluorenes, isotope labeling, metabolites
Abstract:
The dimeric diazofluorenes known as the lomaiviticins are produced by the marine bacterium Salinispora pacifica DPJ-0019. Investigation of the fermentation broth of DPJ-0019 has yielded the first monomeric benzo[b]fluorene isolated from this species, (−)-homoseongomycin (13). (−)-Homoseongomycin (13) is related to the known natural product seongomycin (10), which is co-produced with the monomeric diazofluorenes known as the kinamycins. We describe the synthesis of the isotopically labeled derivative homoseongomycin-d₅ (14), via the intermediacy of the diazofluorene “prelomaiviticin-d₅” (12). Our studies establish that (−)-homoseongomycin (13) may be derived from prelomaiviticin (11) and suggest that 13 and 10 are shunt or detoxification metabolites in lomaiviticin and kinamycin biosynthesis, respectively.
Agid:
5494077