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Squalene–hopene cyclase : final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring
http://hdl.handle.net/10191/25025
http://hdl.handle.net/10191/25025e8bfbdbc-9d6a-47a3-808f-f3e755d7c201
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
2_1456-1470.pdf (2.0 MB)
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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 | Squalene–hopene cyclase : final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring | |||||
| タイトル | ||||||
| タイトル | Squalene–hopene cyclase : final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring | |||||
| 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 |
Hoshino, Tsutomu
× Hoshino, Tsutomu× Nakano, Schin-ichi× Kondo, Tomohiro× Sato, Tsutomu× Miyoshi, Aya |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | To provide insight into the polycyclization mechanism of squalene by squalene–hopene cyclase (SHC) from Alicyclobacilus acidocaldarius, some analogs of nor- and bisnorsqualenes were synthesized including the deuterium-labeled squalenes and incubated with the wild-type SHC, leading to the following inferences. (1) The deprotonation reaction for the introduction of the double bond of the hopene skeleton occurs exclusively from the Z-methyl group on the terminal double bond of squalene. (2) 3R-Oxidosqualene was folded in a boat conformation for the A-ring construction, while the 3S-form was in a chair structure. (3) The terminal two methyl groups are indispensable both for the formation of the 5-membered E-ring of the hopene skeleton and for the initiation of the polycyclization cascade, but the terminal Z-methyl group has a more crucial role for the construction of the 5-membered E-ring than the E-methyl group. (4) Some of the novel terpene skeletons, 36, 37, 39 and 40, were created from the analogs employed in this investigation. | |||||
| 書誌情報 |
Organic & biomolecular chemistry en : Organic & biomolecular chemistry 巻 2, p. 1456-1470, 発行日 2004-12 |
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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/B401172D | |||||
| 著者版フラグ | ||||||
| 値 | publisher | |||||
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Cite as
Hoshino, Tsutomu, Nakano, Schin-ichi, Kondo, Tomohiro, Sato, Tsutomu, Miyoshi, Aya, 2004, Squalene–hopene cyclase : final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring: Royal Society of Chemistry, 1456–1470 p.
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