β-Amyrin Biosynthesis: The Critical Role of Steric Volume at C-19 of 2,3-Oxidosqualene for Its Correct Folding To Generate the Pentacyclic Scaffold
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- Tsutomu Hoshino
- Graduate School of Science and Technology, and Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, Ikarashi 2-8050, Nishi-ku, Niigata 950-2181, Japan
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- Yuki Yamaguchi
- Graduate School of Science and Technology, and Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, Ikarashi 2-8050, Nishi-ku, Niigata 950-2181, Japan
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- Kazunari Takahashi
- Graduate School of Science and Technology, and Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, Ikarashi 2-8050, Nishi-ku, Niigata 950-2181, Japan
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- Ryousuke Ito
- Graduate School of Science and Technology, and Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, Ikarashi 2-8050, Nishi-ku, Niigata 950-2181, Japan
書誌事項
- 公開日
- 2014-06-24
- 資源種別
- journal article
- DOI
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- 10.1021/ol501498q
- 公開者
- American Chemical Society (ACS)
この論文をさがす
説明
The effect of the steric volume at C-19 of (3S)-2,3-oxidosqualene 1 on the polycyclization reaction by β-amyrin synthase was examined. The substrate analogs, in which the methyl group at C-19 of 1 was substituted by an ethyl group and hydrogen atom, were converted into the following three new compounds: (17β-H, 20S)-20-ethyl-dammara-12,24-diene 9, β-amyrin homologue 10, and the 6,6,6,6-fused tetracycle 11. The folding conformations leading to these products are discussed.
収録刊行物
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- Organic Letters
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Organic Letters 16 (13), 3548-3551, 2014-06-24
American Chemical Society (ACS)
