Insights into the complex biosynthesis of the leupyrrins in Sorangium cellulosum So ce690.
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Authors
Kopp, MarenIrschik, Herbert
Gemperlein, Katja
Buntin, Kathrin
Meiser, Peter
Weissman, Kira J
Bode, Helge B
Müller, Rolf
Issue Date
2011-05
Metadata
Show full item recordAbstract
The anti-fungal leupyrrins are secondary metabolites produced by several strains of the myxobacterium Sorangium cellulosum. These intriguing compounds incorporate an atypically substituted γ-butyrolactone ring, as well as pyrrole and oxazolinone functionalities, which are located within an unusual asymmetrical macrodiolide. Previous feeding studies revealed that this novel structure arises from the homologation of four distinct structural units, nonribosomally-derived peptide, polyketide, isoprenoid and a dicarboxylic acid, coupled with modification of the various building blocks. Here we have attempted to reconcile the biosynthetic pathway proposed on the basis of the feeding studies with the underlying enzymatic machinery in the S. cellulosum strain So ce690. Gene products can be assigned to many of the suggested steps, but inspection of the gene set provokes the reconsideration of several key transformations. We support our analysis by the reconstitution in vitro of the biosynthesis of the pyrrole carboxylic starter unit along with gene inactivation. In addition, this study reveals that a significant proportion of the genes for leupyrrin biosynthesis are located outside the core cluster, a 'split' organization which is increasingly characteristic of the myxobacteria. Finally, we report the generation of four novel deshydroxy leupyrrin analogues by genetic engineering of the pathway.Citation
Insights into the complex biosynthesis of the leupyrrins in Sorangium cellulosum So ce690. 2011, 7 (5):1549-63 Mol BiosystAffiliation
Helmholtz Institute for Pharmaceutical Research, Helmholtz Center for Infection Research and Department of Pharmaceutical Biotechnology, Saarland University, PO Box 151150, 66041 Saarbrücken, Germany.Journal
Molecular bioSystemsPubMed ID
21365089Type
ArticleLanguage
enISSN
1742-2051ae974a485f413a2113503eed53cd6c53
10.1039/c0mb00240b
Scopus Count
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