Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 1228-1232Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.121
Keywords
biomimetic synthesis; biosynthesis; heronapyrroles; microbial biodiscovery; natural products; nitropyrroloterpenes
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Funding
- Fonds der Chemischen Industrie (FCI)
- Institute for Molecular Bioscience
- University of Queensland
- Australian Research Council [ARC DP120100183]
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The heronapyrroles A-C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A-C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.
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