Cis or trans with class II diterpene cyclases. Issue 15 (24th March 2017)

• Record Type: Journal Article
• Authors: Jia, Meirong; Peters, Reuben J.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 15(2017)
• Page Start: 3158
• Page End: 3160
• Publication Date: 2017-03-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00510e
• Languages: English
• ISSNs: 1477-0520

Abstract

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. 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 13 E-trans -decalin bicycles, will also act upon ( Z, Z, Z )-nerylneryl diphosphate, producing novel 13 Z-cis -decalin bicycles instead.