Stereochemistry of Water Addition in Triterpene Synthesis:  The Structure of Arabidiol

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 constr...

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Bibliographic Details
Published in:Organic letters 2007-05, Vol.9 (11), p.2183-2186
Main Authors: Kolesnikova, Mariya D, Obermeyer, Allie C, Wilson, William K, Lynch, David A, Xiong, Quanbo, Matsuda, Seiichi P. T
Format: Article
Language:English
Subjects:
Arabidopsis - enzymology
Models, Molecular
Molecular Structure
Triterpenes - chemical synthesis
Water - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070709b