Cyclization mechanism of phomopsene synthase : mass spectrometry based analysis of various site-specifically labeled terpenes
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Elucidation of the cyclization mechanism catalyzed by terpene synthases is important for the rational engineering of terpene cyclases. We developed a chemoenzymatic method for the synthesis of systematically deuterium-labeled geranylgeranyl diphosphate ( GGPP), starting from site-specifically deuterium-labeled isopentenyl diphosphates (IPPs) using IPP isomerase and three prenyltransferases. We examined the cyclization mechanism of tetracyclic diterpene phomopsene with phomopsene synthase. A detailed EI-MS analysis of phomopsene labeled at various positions allowed us to propose the structures corresponding to the most intense peaks, and thus elucidate a cyclization mechanism involving double 1,2-alkyl shifts and a 1,2-hydride shift via a dolabelladien-15-yl cation. Our study demonstrated that this newly developed method is highly sensitive and provides sufficient information for a reliable assignment of the structures of fragmented ions.
収録刊行物
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- Journal of antibiotics
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Journal of antibiotics 70 (5), 632-638, 2017-05
日本抗生物質学術協議会
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詳細情報 詳細情報について
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- CRID
- 1050001202944089088
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- NII論文ID
- 120006360075
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- HANDLE
- 2115/67522
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- ISSN
- 00218820
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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- IRDB
- CiNii Articles