Biochemistry, Biophysics and Molecular Biology, Roy J. Carver Department of
Journal or Book Title
Organic & Biomolecular Chemistry
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.
The Royal Society of Chemistry
Jia, Meirong and Peters, Reuben J., "cis or trans with class II diterpene cyclases" (2017). Biochemistry, Biophysics and Molecular Biology Publications. 254.