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A Family of Related Fungal and Bacterial Di- and Sesterterpenes: Studies on Fusaterpenol and Variediene.
ChemBioChem ( IF 2.6 ) Pub Date : 2019-11-07 , DOI: 10.1002/cbic.201900462
Jan Rinkel 1 , Simon T Steiner 1 , Guangkai Bian 2 , Rong Chen 2 , Tiangang Liu 2 , Jeroen S Dickschat 1
Affiliation  

The absolute configuration of fusaterpenol (GJ1012E) has been revised by an enantioselective deuteration strategy. A bifunctional enzyme with a terpene synthase and a prenyltransferase domain from Aspergillus brasiliensis was characterised as variediene synthase, and the absolute configuration of its product was elucidated. The uniform absolute configurations of these and structurally related di- and sesterterpenes together with a common stereochemical course for the geminal methyl groups of GGPP unravel a similar conformational fold of the substrate in the active sites of the terpene synthases. For variediene, a thermal reaction observed during GC/MS analysis was studied in detail for which a surprising mechanism was uncovered.

中文翻译:


相关真菌和细菌二萜和二倍萜家族:Fusaterpenol 和 Variediene 的研究。



Fusaterpenol (GJ1012E) 的绝对构型已通过对映选择性氘化策略进行了修改。来自巴西曲霉的具有萜烯合酶和异戊烯基转移酶结构域的双功能酶被表征为多烯合酶,并阐明了其产物的绝对构型。这些以及结构相关的二萜和二酯萜的统一绝对构型以及 GGPP 孪生甲基的共同立体化学过程揭示了萜烯合酶活性位点中底物的类似构象折叠。对于异丁烯,我们详细研究了 GC/MS 分析过程中观察到的热反应,并揭示了令人惊讶的机制。
更新日期:2019-11-07
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