Format

Send to

Choose Destination
See comment in PubMed Commons below
Org Biomol Chem. 2017 Mar 28;15(13):2823-2830. doi: 10.1039/c7ob00296c.

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

Author information

1
Department of Chemistry, State University of New York, College of Environmental Science and Forestry, Syracuse, NY 13210, USA. 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.

PMID:
28287229
DOI:
10.1039/c7ob00296c
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for Royal Society of Chemistry
    Loading ...
    Support Center