cis or trans with class II diterpene cyclases.
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.
Roy J. Carver Department of Biochemistry, Biophysics & Molecular Biology, Iowa State University, Ames, IA 50010, USA. rjpeters@iastate.edu.
Meirong
M
Jia
Reuben J
RJ
Peters
D004224:Diterpenes / Q000737:chemistry* / Q000378:metabolism*; D008190:Lyases / Q000378:metabolism*; D013237:Stereoisomerism
D004224:Diterpenes; D008190:Lyases