Back to Search
Start Over
Biosynthesis of Versipelostatin: Identification of an Enzyme-Catalyzed [4+2]-Cycloaddition Required for Macrocyclization of Spirotetronate-Containing Polyketides
- Source :
- Journal of the American Chemical Society
- Publication Year :
- 2014
- Publisher :
- American Chemical Society, 2014.
-
Abstract
- Versipelostatin (VST) is an unusual 17-membered macrocyclic polyketide product that contains a spirotetronate skeleton. In this study, the entire VST biosynthetic gene cluster (vst) spanning 108 kb from Streptomyces versipellis 4083-SVS6 was identified by heterologous expression using a bacterial artificial chromosome vector. Here, we demonstrate that an enzyme, VstJ, catalyzes the stereoselective [4+2]-cycloaddition between the conjugated diene and the exocyclic olefin of a newly identified tetronate-containing intermediate to form the spirotetronate skeleton during VST biosynthesis.
- Subjects :
- Stereochemistry
Oligosaccharides
Biochemistry
Catalysis
Substrate Specificity
chemistry.chemical_compound
Polyketide
Colloid and Surface Chemistry
Biosynthesis
Gene cluster
Spiro Compounds
chemistry.chemical_classification
Bacterial artificial chromosome
Cycloaddition Reaction
Communication
Stereoisomerism
General Chemistry
Cycloaddition
Streptomyces
Enzyme
chemistry
Multigene Family
Polyketides
Biocatalysis
Stereoselectivity
Heterologous expression
Macrolides
Subjects
Details
- Language :
- English
- ISSN :
- 15205126 and 00027863
- Volume :
- 137
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....412caff2e6127b09cacbdf4d3c935524