Sequential Enzymatic Epoxidation Involved in Polyether Lasalocid Biosynthesis
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- 作者：Atsushi Minami ; Mayu Shimaya ; Gaku Suzuki ; Akira Migita ; Sandip S. Shinde ; Kyohei Sato ; Kenji Watanabe ; Tomohiro Tamura ; Hiroki Oguri ; Hideaki Oikawa
- 刊名：The Journal of the American Chemical Society
- 出版年：2012
- 出版时间：May 2, 2012
- 年：2012
- 卷：134
- 期：17
- 页码：7246-7249
- 全文大小：276K
- 年卷期：v.134,no.17(May 2, 2012)
- ISSN：1520-5126
文摘
Enantioselective epoxidation followed by regioselective epoxide opening reaction are the key processes in construction of the polyether skeleton. Recent genetic analysis of ionophore polyether biosynthetic gene clusters suggested that flavin-containing monooxygenases (FMOs) could be involved in the oxidation steps. In vivo and in vitro analyses of Lsd18, an FMO involved in the biosynthesis of polyether lasalocid, using simple olefin or truncated diene of a putative substrate as substrate mimics demonstrated that enantioselective epoxidation affords natural type mono- or bis-epoxide in a stepwise manner. These findings allow us to figure out enzymatic polyether construction in lasalocid biosynthesis.