Campus Units

Biochemistry, Biophysics and Molecular Biology, Roy J. Carver Department of

Document Type

Article

Publication Version

Accepted Manuscript

Publication Date

2017

Journal or Book Title

Organic & Biomolecular Chemistry

Volume

15

Issue

15

First Page

3158

Last Page

3160

DOI

10.1039/C7OB00510E

Abstract

Isoprenoid precursors readily undergo (poly)cyclization in electrophilic reaction cascades, presumably as internal addition of the carbon–carbon double-bonds from neighboring isoprenyl repeats readily forms relatively stable cyclohexyl tertiary carbocation intermediates. This hypothesis is agnostic regarding alkene configuration (i.e., Z or E). Consistent with this, here it is shown that certain class II diterpene cyclases, which normally convert (E,E,E)-geranylgeranyl diphosphate to 13E-trans-decalin bicycles, will also act upon (Z,Z,Z)-nerylneryl diphosphate, producing novel 13Z-cis-decalin bicycles instead.

Comments

This is a manuscript of an article published as Jia, Meirong, and Reuben J. Peters. "cis or trans with class II diterpene cyclases." Organic & biomolecular chemistry 15, no. 15 (2017): 3158-3160. doi: 10.1039/C7OB00510E. Posted with permission.

Copyright Owner

The Royal Society of Chemistry

Language

en

File Format

application/pdf

Published Version

Share

COinS