Biotechnology Research Center, The University of Tokyo , 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
J Am Chem Soc. 2014 Apr 2;136(13):4837-40. doi: 10.1021/ja500270m. Epub 2014 Mar 18.
A cyclolavandulyl group is a C10 monoterpene with a branched and cyclized carbon skeleton. This monoterpene is rarely found in nature, and its biosynthesis is poorly understood. To determine the biosynthesis mechanism of this monoterpene, we sequenced the genome of Streptomyces sp. CL190, which produces lavanducyanin, a phenazine with an N-linked cyclolavandulyl structure. Sequencing and homology searches identified one candidate gene product that consists of only a cis-isoprenyl diphosphate synthase domain. Disruption of the gene and biochemical analysis of the recombinant enzyme demonstrated that the enzyme synthesized a cyclolavandulyl diphosphate essential for the biosynthesis of lavanducyanin. This enzyme is an unprecedented terpene synthase that catalyzes both the condensation of the C5 isoprene units and subsequent cyclization to form the cyclolavandulyl monoterpene structure.
环lavandulyl 基团是一个 C10 单萜烯，具有分支和环化的碳骨架。这种单萜烯在自然界中很少见，其生物合成也知之甚少。为了确定这种单萜烯的生物合成机制，我们对产生 lavanducyanin 的链霉菌 sp. CL190 进行了基因组测序，lavanducyanin 是一种具有 N 连接的环 lavandulyl 结构的 phenazine。测序和同源搜索确定了一个候选基因产物，它仅由顺式异戊二烯二磷酸合酶结构域组成。该基因的破坏和重组酶的生化分析表明，该酶合成了 lavanducyanin 生物合成所必需的环 lavandulyl 二磷酸。这种酶是一种前所未有的萜烯合酶，可催化 C5 异戊二烯单元的缩合以及随后的环化，形成环 lavandulyl 单萜烯结构。
