8α-hydroxypolypoda-13,17,21-triene | 591215-31-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 8α-hydroxypolypoda-13,17,21-triene
• 英文别名: (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• CAS: 591215-31-5
• 化学式: C₃₀H₅₂O
• 分子量: 428.742
• InChiKey: GGYNVIDANVHEJO-GPHXDKKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8α-hydroxypolypoda-13,17,21-triene 在 potassium permanganate 、 四丁基溴化铵 作用下， 以 水 、 苯 为溶剂， 生成 (+)-ambreinolide
  参考文献：
  名称：

  Isolation from Pistacia resins of a bicyclic triterpenoid representing an apparent trapped intermediate of squalene 2,3-epoxide cyclization

  摘要：

  DOI：

  10.1021/ja00320a064
• 作为产物：
  描述：

  (8R)-3β,8-dihydroxypolypoda-13E,17E,21-triene 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 8α-hydroxypolypoda-13,17,21-triene
  参考文献：
  名称：

  Isolation from Pistacia resins of a bicyclic triterpenoid representing an apparent trapped intermediate of squalene 2,3-epoxide cyclization

  摘要：

  DOI：

  10.1021/ja00320a064

文献信息

• Analysis of the Catalytic Mechanism of Bifunctional Triterpene/Sesquarterpene Cyclase: Tyr167 Functions To Terminate Cyclization of Squalene at the Bicyclic Step
  作者：Liudmila Tenkovskaia、Mizuki Murakami、Kotone Okuno、Daijiro Ueda、Tsutomu Sato

  DOI：10.1002/cbic.201700329

  日期：2017.10.5

  (bifunctional C30/C35 terpene cyclase) is analyzed for the first time by using mutant enzymes. The mutant enzyme Y167A produces tricyclic triterpene from C30 squalene. The bulk size at the Y167 position is significant for termination of the cyclization of squalene at the bicyclic step.

  大小问题：使用突变酶首次分析了类癌合酶（双功能C 30 / C 35萜烯环化酶）的催化机理。突变酶Y167A从C 30角鲨烯生产三环三萜。在Y167位置的体积对于在双环步骤终止角鲨烯的环化是重要的。
• Total synthesis of (±)-6α-hydroxyachilla-9,13,17,21-tetraene and (±)-8α-hydroxypolypoda-13,17,21-triene
  作者：Mugio Nishizawa、Hiroko Takao、Naoko Kanoh、Kohsuke Asoh、Susumi Hatakeyama、Hidetoshi Yamada

  DOI：10.1016/s0040-4039(00)77281-9

  日期：1994.8

  Novel triterpene alcohols with achillane and polypodane skeletons isolated from Polypodiaceae fern have been synthesized on the basis of inter and intramolecular trapping of cationic intermediates of the biomimetic olefin cyclization.

  从仿生植物蕨类植物中分离出具有a烷和多聚环烷骨架的新型三萜醇，是基于仿生烯烃环化的阳离子中间体的分子间和分子内捕获而合成的。
• Cyclization of Squalene from Both Termini: Identification of an Onoceroid Synthase and Enzymatic Synthesis of Ambrein
  作者：Daijiro Ueda、Tsutomu Hoshino、Tsutomu Sato

  DOI：10.1021/ja4107226

  日期：2013.12.11

  The onoceroids are triterpenoids biosynthesized from squalene or (3S)-2,3-oxidosqualene by cyclization from both termini. We recently revealed that tetraprenyl-beta-curcumene cyclase from Bacillus megaterium (BmeTC) is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail tetraprenyl-beta-curcumene and tail-to-tail squalene into pentacyclic and bicyclic products, respectively, in vivo. Here, we reveal that BmeTC has an unprecedented catalytic function in cyclizing squalene from both termini and is the first onoceroid synthase. We also report the first onoceroids from bacterial origin. Our discoveries suggest that symmetric and asymmetric onoceroids could be biosynthesized by a single enzyme via an intermediate cyclized at one terminus of squalene. Furthermore, the new function of BmeTC enabled the synthesis of (+)-ambrein, a major constituent of ambergris that is difficult to obtain naturally, via a mutated squalene-hopene cyclase-catalyzed reaction from easily available squalene.