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Cis or trans with class II diterpene cyclases.

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.

SUBMITTER: Jia M

PROVIDER: S-EPMC5441681 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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cis or trans with class II diterpene cyclases.

Jia Meirong M Peters Reuben J RJ

Organic & biomolecular chemistry 20170401 15

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-d ...[more]

PMID: 28338699

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Cis-trans

Project description:Cis-trans

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