利科桑塔隆醇的生物合成,这是一个由cis-prenyl衍生的双化物
Jiachen Zi1, Yuki Matsuba, Young J Hong
1Department of Biochemistry, Biophysics, and Molecular Biology, Iowa State University , Ames, Iowa 50011, United States.
Journal of the American Chemical Society
|November 19, 2014
概括
这项研究确定了番茄中一种cisoid diterpenoid的新生物合成途径,从 (Z,Z,Z) -nerylneryl diphosphate开始. 它揭示了独特的循环和氧化步骤,提供了对类生物合成的机械洞察力.
科学领域:
- 自然产品化学 自然产品化学
- 植物生物化学 植物生物化学
- 有机合成 有机合成
背景情况:
- 类天然产品通常来源于转化配置的异二酸盐前体.
- 此前还没有发现任何由cisoid前体 (Z,Z,Z) -nerylneryl diphosphate (1) 衍生而来的diterpenoids.
- 研究新的生物合成途径对于理解自然产品多样性至关重要.
研究的目的:
- 在番茄中识别和描述一种新的类生物合成途径.
- 为了阐明从 (Z,Z,Z) - 尼里尔尼里尔二酸盐 (1) 来生成一个化物二化物的起源.
- 为了获得对这种途径所涉及的独特化学转换的机械洞察力.
主要方法:
- 来自番茄的类生物合成基因集群的分析.
- 化学合成和介质化合物的表征.
- 量子化学计算用于研究反应机制.
- 氧气标记研究,以追踪代谢转变.
主要成果:
- 来自 (Z,Z,Z) - 尼林尼林二酸盐 (1) 的路径的识别.
- 发现了lycosantalene (2),这是一种具有三基核的二基,通过循环形成的1.
- 通过环氧介质 (3) 将 2 中的 cis 双键转化为 α-基部分的解析.
- 使用氧气标记,证明了3的氧化转化为色醇 (4).
结论:
- 这项工作阐明了可桑达的化物起源 (4).
- 透露了类生物合成中的新型循环和氧化机制.
- 这些发现扩大了我们对植物天然产品生物合成的理解.
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