Document Detail


Biosynthesis of diazepinomicin/ECO-4601, a Micromonospora secondary metabolite with a novel ring system.
MedLine Citation:
PMID:  18722414     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
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:
Type:  Journal Article     Date:  2008-08-23
Journal Detail:
Title:  Journal of natural products     Volume:  71     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-09-29     Completed Date:  2008-11-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1585-90     Citation Subset:  IM    
Affiliation:
Thallion Pharmaceuticals Inc., 7150 Alexander-Fleming, Montréal, Québec, H4S 2C8, Canada. jmcalpine@thallion.com
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MeSH Terms
Descriptor/Qualifier:
Alkaloids / chemical synthesis*,  chemistry
Cyclization
Dibenzazepines / chemical synthesis*,  chemistry
Micromonospora / chemistry*,  genetics
Molecular Structure
Chemical
Reg. No./Substance:
0/Alkaloids; 0/Dibenzazepines; 0/diazepinomicin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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