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Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway

Riclea, Ramona ; Aigle, Bertrand ; Leblond, Pierre ; Schoenian, Ilka ; Spiteller, Dieter ; Dickschat, Jeroen S. Spiteller, Dieter ; Dickschat, Jeroen

Chembiochem : a European journal of chemical biology, 2012-07, Vol.13 (11), p.1635-1644 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

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Título:
Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway
Autor: Riclea, Ramona ; Aigle, Bertrand ; Leblond, Pierre ; Schoenian, Ilka ; Spiteller, Dieter ; Dickschat, Jeroen S.
Spiteller, Dieter ; Dickschat, Jeroen
Assuntos: 4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - analysis ; 4-Butyrolactone - chemical synthesis ; Antimycin A - analogs & derivatives ; Antimycin A - biosynthesis ; Antimycin A - chemistry ; Antimycin A - metabolism ; biosynthesis ; Biosynthetic Pathways ; Chromatography, High Pressure Liquid ; Gas Chromatography-Mass Spectrometry ; GC-MS ; lactones ; Life Sciences ; Molecular Structure ; Spectrometry, Mass, Electrospray Ionization ; Streptomyces - chemistry ; Streptomyces - genetics ; Streptomyces - metabolism ; streptomycetes ; synthesis
É parte de: Chembiochem : a European journal of chemical biology, 2012-07, Vol.13 (11), p.1635-1644
Notas: Deutsche Forschungsgemeinschaft - No. DI1536/1-2; No. SP1106/3-1; No. DI1536/3-1
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Descrição: 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 A3b, 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. Knock it out! 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.
Editor: Weinheim: WILEY-VCH Verlag
Idioma: Inglês

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Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway

Riclea, Ramona ; Aigle, Bertrand ; Leblond, Pierre ; Schoenian, Ilka ; Spiteller, Dieter ; Dickschat, Jeroen S. Spiteller, Dieter ; Dickschat, Jeroen

Weinheim: WILEY-VCH Verlag

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