Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis

José-Luis Giner; Ju Feng

doi:10.1039/C7OB00296C

Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis

José-Luis Giner*^a and Ju Feng^a

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* Corresponding authors

^a Department of Chemistry, State University of New York, College of Environmental Science and Forestry, Syracuse, USA
E-mail: jlginer@syr.edu

Abstract

The squalene cyclase of Tetrahymena pyriformis cyclizes 2,3-dihydrosqualene to euph-7-ene. This was used as a model for euphane biosynthesis. D-ring formation was demonstrated to involve pre-chair folding through an experiment with 2,3-dihydro-5-oxasqualene. This requires that a non-least motion rotation (120°) of the C17–20 bond in the intermediate deoxydammaranyl cation occurs before the first 1,2-hydride shift. Truncated substrates relieved the hindrance associated with this rotation and permitted a least motion pathway. Several triterpenes were found to be minor products of the Tetrahymena cyclase.

This article is part of the themed collection: Polycyclic Reactions in Synthesis and Biosynthesis

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Publication details

The article was received on 07 Feb 2017, accepted on 07 Mar 2017 and first published on 13 Mar 2017

Article type: Paper

DOI: 10.1039/C7OB00296C

Citation: Org. Biomol. Chem., 2017,15, 2823-2830

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Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis

J. Giner and J. Feng, Org. Biomol. Chem., 2017, 15, 2823
DOI: 10.1039/C7OB00296C
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Organic & Biomolecular Chemistry

Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis

Abstract

Supplementary files

Publication details

Stereochemical investigations of the Tetrahymena cyclase, a model system for euphane/tirucallane biosynthesis

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