Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species.
Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species.
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通过从非致病性分枝杆菌中获得的 Z 型 C35-聚异戊二烯二磷酸酯的环化，生物合成新型环状 C35-萜烯。
DOI：
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发表时间：
2008
影响因子：
3.2
通讯作者：
T. Hoshino
中科院分区：
文献类型：
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作者：
Tsutomu Sato;Atsushi Kigawa;R. Takagi;T. Adachi;T. Hoshino
对 12 种非致病性分枝杆菌的脂质成分进行了分析。从 3 个物种中获得了一种新型环状 C(35)-萜烯，命名为 heptaprenylcycline ，而从 6 个物种中获得了具有 3 个 Z-双键的八氢庚烯醇 。培养细胞中 和 的量在 4 至 6 天的稳定期后增加。在 37 摄氏度的较高温度下， 的产率明显高于最佳温度 28 摄氏度，而 的产率在所有温度下都保持不变。 d-[1-(13)C]葡萄糖喂养实验表明，d-[1-(13)C]葡萄糖是通过异戊烯二磷酸产生的，异戊烯二磷酸是糖酵解和甲基赤藓糖醇磷酸途径的代谢产物。使用氯酚分枝杆菌的无细胞提取物成功地将八氢庚烯基二磷酸转化为 ，证明它是 的生物合成中间体。这是通过线性 C(35)-类异戊二烯的环化来生物合成天然萜的第一个例子。 C(35)-萜烯环化酶的底物具有Z型异戊二烯基部分；然而，萜烯环化酶通常使用E型类异戊二烯。尚未检测到编码萜烯环化酶的基因，该萜烯环化酶可环化含有 Z-双键作为天然底物的异戊二烯基二磷酸。尽管使用 FASTA3 程序进行了仔细搜索，但我们无法在 M. vanbaalenii 基因组中检测到任何与已知二磷酸触发类型的单萜、倍半萜和二萜环化酶同源的基因，其 DNA 序列最近已被阐明。这表明非致病性分枝杆菌中可能存在一种新型萜烯环化酶。
Lipid components from 12 nonpathogenic Mycobacterium species were analysed. A novel cyclic C(35)-terpene, named heptaprenylcycline , was obtained from 3 species, while octahydroheptaprenol , which has 3 Z-double bonds, was obtained from 6 species. The amounts of and in the cultured cells increased after the 4- to 6-d stationary phase. The yield of was considerably greater at a higher temperature of 37 degrees C than at an optimal temperature of 28 degrees C, while that of remained unchanged at all temperatures. A feeding experiment with d-[1-(13)C]glucose revealed that was produced via isopentenyl diphosphate, which is a metabolite of glycolysis and the methylerythritol phosphate pathway. The conversion of octahydroheptaprenyl diphosphate to was successful by using the cell-free extracts of M. chlorophenolicum, demonstrating that is the biosynthetic intermediate of . This is the first example of the biosynthesis of a natural terpene via the cyclisation of a linear C(35)-isoprenoid. The substrate for C(35)-terpene cyclase has Z-type prenyl moieties; however, terpene cyclases usually employ E-type isoprenoids. The gene encoding the terpene cyclase that cyclises prenyl diphosphate containing Z-double bonds as the natural substrate has not yet been detected. Despite a careful search using the FASTA3 program, we could not detect any gene that is homologous to the known diphosphate-triggered type of mono-, sesqui- and diterpene cyclases in the genome of M. vanbaalenii, the DNA sequence of which has recently been elucidated. This suggests that a novel type of terpene cyclase might exist in the nonpathogenic Mycobacterium species.
DOI：
10.1073/pnas.0401657101
发表时间：
2004-09-14
影响因子：
11.1
作者：
Pethe, K;Swenson, DL;Russell, DG
通讯作者：
Russell, DG