Heronapyrrole D: a case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

Schmidt, Jens, Khalil, Zeinab, Capon, Robert J. and Stark, Christian B. W. (2014) Heronapyrrole D: a case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery. Beilstein Journal of Organic Chemistry, 10 1228-1232. doi:10.3762/bjoc.10.121


Author Schmidt, Jens
Khalil, Zeinab
Capon, Robert J.
Stark, Christian B. W.
Title Heronapyrrole D: a case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery
Journal name Beilstein Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1860-5397
Publication date 2014-05-26
Sub-type Article (original research)
DOI 10.3762/bjoc.10.121
Open Access Status DOI
Volume 10
Start page 1228
End page 1232
Total pages 5
Place of publication Frankfurt am Main, Germany
Publisher Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
Language eng
Abstract 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.
Keyword Biomimetic synthesis
Biosynthesis
Heronapyrroles
Microbial biodiscovery
Natural products
Nitropyrroloterpenes
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Institute for Molecular Bioscience - Publications
 
Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 15 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 15 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Created: Tue, 17 Jun 2014, 10:32:58 EST by System User on behalf of Institute for Molecular Bioscience