Accumulation of an E,E,E-Triene by the Monensin-Producing Polyketide Synthase when Oxidative Cyclization is Blocked

Accumulation of an E,E,E-Triene by the Monensin-Producing Polyketide Synthase when Oxidative Cyclization is Blocked

Evidence for the intermediate in the polyether biosynthesis of the ionophore antibiotic monensin A has been obtained. A tridecaketide E,E,E‐triene (see formula) has been isolated by using mutant strains of Streptomyces cinnamonensis. Characterization of this intermediate allows the likely biosynthet...

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Veröffentlicht in:Angewandte Chemie International Edition 2005-11, Vol.44 (43), p.7075-7078
Hauptverfasser: Bhatt, Apoorva, Stark, Christian B. W., Harvey, Barbara M., Gallimore, Andrew R., Demydchuk, Yuliya A., Spencer, Jonathan B., Staunton, James, Leadlay, Peter F.
Format: Artikel
Sprache:eng
Schlagworte:
biosynthesis
Cyclization
epoxidases
Molecular Conformation
Monensin - analogs & derivatives
Monensin - biosynthesis
Monensin - chemistry
natural products
Oxidation-Reduction
Polyenes - chemistry
polyethers
Polyketide Synthases - chemistry
protein engineering
Stereoisomerism
Streptomyces - enzymology
Streptomyces - genetics
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Beschreibung
Zusammenfassung:Evidence for the intermediate in the polyether biosynthesis of the ionophore antibiotic monensin A has been obtained. A tridecaketide E,E,E‐triene (see formula) has been isolated by using mutant strains of Streptomyces cinnamonensis. Characterization of this intermediate allows the likely biosynthetic route to monensin to be discriminated.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200501757