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Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway

ChemBioChem, 23 July 2012, Vol.13(11), pp.1635-1644 [Peer Reviewed Journal]

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  • Title:
    Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway
  • Author: Riclea, R. ; Aigle, B. ; Leblond, P. ; Schoenian, I. ; Spiteller, D. ; Dickschat, J.S.
  • Found In: ChemBioChem, 23 July 2012, Vol.13(11), pp.1635-1644 [Peer Reviewed Journal]
  • Subjects: Biosynthesis ; Gc-MS ; Lactones ; Streptomycetes ; Synthesis
  • Rights: Copyright 2013 Elsevier B.V., All rights reserved. ; MEDLINE® is the source for the MeSH terms of this document.
  • Description: The volatiles released by several streptomycetes were collected by using a closed‐loop stripping apparatus (CLSA) and analysed by GC–MS. The obtained headspace extracts of various species contained blastmycinone, a known degradation product of the fungicidal antibiotic, antimycin A, and several unknown derivatives. The suggested structures of these compounds, based on their mass spectra and GC retention indices, were confirmed by comparison to synthetic reference samples. Additional compounds found in the headspace extracts were butenolides formed from the blastmycinones by elimination of the carboxylic acid moiety. Analysis of a gene knockout mutant in the antimycin biosynthetic gene cluster demonstrated that all blastmycinones and butenolides are formed via the antimycin biosynthetic pathway. The structural variation of the blastmycinones identified here is much larger than within the known antimycins, thus suggesting that several antimycin derivatives remain to be discovered. Several volatile lactones have been found in streptomycetes. Their structures have been suggested based on GC–MS data and verified by comparison with synthetic standards. The origin of all lactones was shown in knockout experiments to depend on the antimycin biosynthetic gene cluster.
  • Identifier: ISSN: 14394227 ; E-ISSN: 14397633 ; DOI: 10.1002/cbic.201200260

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