Kekulé-Institute for Organic Chemistry and Biochemistry , University of Bonn , Gerhard-Domagk-Strasse 1 , 53121 Bonn , Germany.
Org Lett. 2019 Dec 6;21(23):9442-9445. doi: 10.1021/acs.orglett.9b03654. Epub 2019 Nov 8.
As a member of a large phylogenetic clade of enzymes in , a terpene synthase from is functionally characterized to produce micromonocyclol. This diterpene alcohol features a rare 15-membered ring, which prevented elucidation of the only stereocenter by labeling experiments. This problem was addressed by chemical transformation into bicyclic brominated derivatives, whose rigidified skeletons allowed for a stereochemical assignment. Using this strategy, a complete stereochemical model of the cyclization mechanism was also elaborated.
作为一类大型酶的系统发育枝成员，从 中分离到一种萜烯合酶，该酶具有功能特征，可以产生 micromonocyclol。这种二萜醇具有罕见的 15 元环，这使得通过标记实验阐明唯一的手性中心变得困难。通过化学转化为双环溴代衍生物来解决这个问题，其刚性骨架允许进行立体化学分配。使用这种策略，还详细阐述了环化机制的完整立体化学模型。
