| Biosynthesis of diazepinomicin/ECO-4601, a Micromonospora secondary metabolite with a novel ring system. | |
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MedLine Citation:
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PMID: 18722414 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The novel microbial metabolite diazepinomicin/ECO-4601 (1) has a unique tricyclic dibenzodiazepinone core, which was unprecedented among microbial metabolites. Labeled feeding experiments indicated that the carbocyclic ring and the ring nitrogen of tryptophan could be incorporated via degradation to the 3-hydroxyanthranilic acid, forming ring A and the nonamide nitrogen of 1. Genomic analysis of the biosynthetic locus indicated that the farnesyl side chain was mevalonate derived, the 3-hydroxyanthranilic acid moiety could be formed directly from chorismate, and the third ring was constructed via 3-amino-5-hydroxybenzoic acid. Successful incorporation of 4,6-D2-3-hydroxyanthranilic acid into ring A of 1 via feeding experiments supports the genetic analysis and the allocation of the locus to this biosynthesis. These studies highlight the enzymatic complexity needed to produce this structural type, which is rare in nature. |
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Authors:
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James B McAlpine; Arjun H Banskota; Romila D Charan; Gerhard Schlingmann; Emmanuel Zazopoulos; Mahmood Piraee; Jeffrey Janso; Valerie S Bernan; Mustapha Aouidate; Chris M Farnet; Xidong Feng; Zhizi Zhao; Guy T Carter |
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Publication Detail:
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Type: Journal Article Date: 2008-08-23 |
Journal Detail:
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Title: Journal of natural products Volume: 71 ISSN: 1520-6025 ISO Abbreviation: J. Nat. Prod. Publication Date: 2008 Sep |
Date Detail:
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Created Date: 2008-09-29 Completed Date: 2008-11-12 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7906882 Medline TA: J Nat Prod Country: United States |
Other Details:
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Languages: eng Pagination: 1585-90 Citation Subset: IM |
Affiliation:
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Thallion Pharmaceuticals Inc., 7150 Alexander-Fleming, Montréal, Québec, H4S 2C8, Canada. jmcalpine@thallion.com |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkaloids
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chemical synthesis*,
chemistry Cyclization Dibenzazepines / chemical synthesis*, chemistry Micromonospora / chemistry*, genetics Molecular Structure |
| Chemical | |
Reg. No./Substance:
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0/Alkaloids; 0/Dibenzazepines; 0/diazepinomicin |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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