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Controlling a structural branch point in ergot alkaloid biosynthesis
- Source :
- Journal of the American Chemical Society. 132(37)
- Publication Year :
- 2010
-
Abstract
- The ergot alkaloids are a diverse class of fungal-derived indole alkaloid natural products with potent pharmacological activities. The biosynthetic intermediate chanoclavine-I aldehyde 1 represents a branch point in ergot biosynthesis. Ergot alkaloids festuclavine 2 and agroclavine 3 derive from alternate enzymatic pathways originating from the common biosynthetic precursor chanoclavine-I aldehyde 1. Here we show that while the Old Yellow Enzyme homologue EasA from the ergot biosynthetic gene cluster of Aspergillus fumigatus acts on chanoclavine-I aldehyde 1 to yield festuclavine 2, EasA from Neotyphodium lolii, in contrast, produces agroclavine 3. Mutational analysis suggests a mechanistic rationale for the switch in activity that controls this critical branch point of ergot alkaloid biosynthesis.
- Subjects :
- Ergot Alkaloids
Stereochemistry
Stereoisomerism
Biochemistry
Catalysis
Article
Aspergillus fumigatus
chemistry.chemical_compound
Colloid and Surface Chemistry
Biosynthesis
Chanoclavine
Gene cluster
Agroclavine
heterocyclic compounds
chemistry.chemical_classification
biology
Indole alkaloid
Sequence Homology, Amino Acid
Chemistry
NADPH Dehydrogenase
General Chemistry
biology.organism_classification
Enzyme
Neotyphodium
Multigene Family
Subjects
Details
- ISSN :
- 15205126
- Volume :
- 132
- Issue :
- 37
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....cdcbb93b4b91f606a8b07fdd006008d8