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Stereochemistry of Water Addition in Triterpene Synthesis: The Structure of Arabidiol
- Source :
- Organic Letters. 9:2183-2186
- Publication Year :
- 2007
- Publisher :
- American Chemical Society (ACS), 2007.
-
Abstract
- An oxidosqualene cyclase from Arabidopsis thaliana makes arabidiol, a tricyclic triterpene reported with indeterminate side-chain stereochemistry. We established the full structure of arabidiol through chemical degradation, NOE experiments, and molecular modeling. By examining the mechanistic constraints that govern water addition in triterpene synthesis, we further show how the stereochemistry of hydroxylation can generally be deduced a priori, why deprotonation is more common than hydroxylation, and why cyclases that perform hydroxylation also generate olefinic byproducts.
- Subjects :
- Models, Molecular
chemistry.chemical_classification
Molecular Structure
Molecular model
biology
Stereochemistry
Organic Chemistry
Arabidopsis
Water
General Medicine
biology.organism_classification
Biochemistry
Triterpenes
Oxidosqualene cyclase
Terpene
Hydroxylation
chemistry.chemical_compound
Deprotonation
chemistry
Triterpene
Organic chemistry
Arabidopsis thaliana
Physical and Theoretical Chemistry
Chemical decomposition
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 9
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....6e622fa078aebf212ef71d108c4ffb2e