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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 |
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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 | ||||||
言語 | en | |||||
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 | ||||||
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 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 14770520 | |||||
書誌レコードID | ||||||
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 |