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cis or trans with class II diterpene cyclases†
Meirong Jia,Reuben J. Peters
Organic & Biomolecular Chemistry Pub Date : 03/21/2017 00:00:00 , DOI:10.1039/C7OB00510E
Abstract

Isoprenoid precursors readily undergo (poly)cyclization in electrophilic reaction cascades, presumably as internal addition of the carbon窶田arbon 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.

Graphical abstract: cis or trans with class II diterpene cyclases
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