(+)-Thalianatriene 和 (-)-Retigeranin B 由拟南芥中的倍半萜合酶催化合成。
(+)-Thalianatriene and (-)-Retigeranin B Catalyzed by Sesterterpene Synthases from Arabidopsis thaliana.
机构信息
Key Laboratory of Synthetic Biology, CAS Center for Excellence in Molecular Plant Sciences, Institute of Plant Physiology and Ecology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences , Shanghai 200032, China.
University of Chinese Academy of Sciences , Beijing 100039, China.
出版信息
Org Lett. 2017 Apr 7;19(7):1816-1819. doi: 10.1021/acs.orglett.7b00586. Epub 2017 Mar 28.
Two GFPPS linked (+)-thalianatriene (1) and (-)-retigeranin B (2) sesterterpene synthase genes were identified from the genome of Arabidopsis thaliana. 1 possesses an unprecedented 11-6-5 tricyclic ring system, while 2 contains a characteristic 5-5-5-6-5 pentacyclic ring system. Their structures were determined by extensive NMR spectroscopy, chemical derivatization, and X-ray crystallography. The variable-temp NMR measurement of 3, a diepoxy-bearing derivative of 1, enables us to completely assign the NMR signals of the two conformers as 3a (67%, UUU) and 3b (33%, UUD). A plausible biosynthesis mechanism of 1 was proposed.
从拟南芥基因组中鉴定出两个 GFPPS 连接的 (+)-thalianatriene（1）和（-）-retigeranin B（2）倍半萜合酶基因。1 具有前所未有的 11-6-5 三环系统，而 2 则包含特征性的 5-5-5-6-5 五环系统。通过广泛的 NMR 光谱、化学衍生化和 X 射线晶体学确定了它们的结构。1 的环氧衍生物 3 的变温 NMR 测量使我们能够完全分配两个构象的 NMR 信号，即 3a（67%，UUU）和 3b（33%，UUD）。提出了 1 的合理生物合成机制。
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