論文 - 詳細
| RRC ID | 89052 |
|---|---|
| 著者 | Abe T, Katano M, Otsuka I, Wakamatsu N, Takahashi S, Ueda D, Fukuda E, Endo S, Nishikawa K, Yasuno Y, Nakayama A, Shinada T, Sato T. |
| タイトル | Isolation and structural determination of natural products bearing tetrahydrogenated isoprenoid side-chains at their ω-termini. |
| ジャーナル | Org Biomol Chem |
| Abstract |
Hydrogenated isoprenoids are found in a range of biologically important natural products, such as isoprenoid quinones, chlorophyll, vitamin E, and dolichol. In this study, a new method was developed for determining the chirality of the tetrahydrogenated isoprenoid (THI) structures of two natural products, namely heptaprenylcycli-14E,18E-diene and (22R,5E,9E,13E,17E)-6,10,14,18,22,26-hexamethylheptacosa-5,9,13,17-tetraen-2-one, for which the chiral carbon centres have never been elucidated. Our research group previously isolated the former sesquarterpene from Mycobacterium chlorophenolicum, while the latter was isolated as a new polyprenyl acetone from Conexibacter woesei in the current study. To determine their chiralities, these two THI-containing terpenoids were subjected to ozonolysis to produce (R)-6,10-dimethyl-2-undecanones. The optically active (S)-6,10-dimethyl-2-undecanone was prepared as an authentic chiral sample by the reduction of (S,E)-6,10-dimethylundeca-3,9-dien-2-one. Chiral high-performance liquid chromatographic analysis of the ozonolysis products and of authentic (S)- and racemic 6,10-dimethyl-2-undecanone samples unambiguously assigned the THI chiral carbon centres of both compounds as R. This new method could be a useful tool for determining the chiralities of other THIs. It is also expected to contribute to our understanding of the biosynthetic mechanisms and biological roles of THIs. |
| 巻・号 | 23(14) |
| ページ | 3423-3430 |
| 公開日 | 2025-4-2 |
| DOI | 10.1039/d5ob00160a |
| PMID | 40079055 |
| MeSH | Biological Products* / chemistry Biological Products* / isolation & purification Molecular Structure Stereoisomerism Terpenes* / chemistry Terpenes* / isolation & purification |
| オルトメトリクス指標 |
オルトメトリクス指標項目
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| 最多言及媒体 | X(Twitter) |
| 各媒体での言及数の合計 | 12 |
| 過去6か月間でのオルトメトリクス指標の変動値 | 0.0 |
| リソース情報 | |
| 一般微生物 | JCM11494 JCM31881 JCM31078 |