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Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species
http://hdl.handle.net/10191/25026
http://hdl.handle.net/10191/250269fec1d02-50a8-4b7b-8df1-5e0f1103fead
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
6_3788-3794.pdf (800.0 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2014-02-07 | |||||
| タイトル | ||||||
| タイトル | Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species | |||||
| タイトル | ||||||
| タイトル | Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species | |||||
| 言語 | en | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源 | http://purl.org/coar/resource_type/c_6501 | |||||
| タイプ | journal article | |||||
| 著者 |
Sato, Tsutomu
× Sato, Tsutomu× Kigawa, Atsushi× Takagi, Ryosuke× Adachi, Tomomi× Hoshino, Tsutomu |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | 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. | |||||
| 書誌情報 |
Organic & biomolecular chemistry en : Organic & biomolecular chemistry 巻 6, p. 3788-3794, 発行日 2008-08 |
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| 出版者 | ||||||
| 出版者 | Royal Society of Chemistry | |||||
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| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 14770520 | |||||
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| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA1168650X | |||||
| DOI | ||||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | info:doi/10.1039/b808513g | |||||
| 著者版フラグ | ||||||
| 値 | publisher | |||||
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Sato, Tsutomu, Kigawa, Atsushi, Takagi, Ryosuke, Adachi, Tomomi, Hoshino, Tsutomu, 2008, Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species: Royal Society of Chemistry, 3788–3794 p.
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