AI Article Synopsis
- A new farnesyl pyrophosphate (FPP) derivative has a shifted double bond and is converted by protoilludene synthase and viridiflorene synthase, resulting in a novel germacrene derivative named "germacrene F."
- The modification in the olefinic double bond changes the initial cyclization process from a 1→11 to a 1→10 mechanism.
- Molecular docking studies provide insight into Omp7's behavior, while temperature-dependent NMR and NOE studies reveal that germacrene F has a preferred mirror-symmetric conformation in its cyclodecane ring.
Article Abstract
The new farnesyl pyrophosphate (FPP) derivative with a shifted olefinic double bond from C6-C7 to C7-C8 is accepted and converted by the sesquiterpene cyclases protoilludene synthase (Omp7) as well as viridiflorene synthase (Tps32). In both cases, a so far unknown germacrene derivative was found to be formed, which we name "germacrene F". Both cases are examples in which a modification around the central olefinic double bond in FPP leads to a change in the mode of initial cyclization (from 1→11 to 1→10). For Omp7 a rationale for this behaviour was found by carrying out molecular docking studies. Temperature-dependent NMR experiments, accompanied by NOE studies, show that germacrene F adopts a preferred mirror-symmetric conformation with both methyl groups oriented in the same directions in the cyclodecane ring.
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