(+)-onoceranoxide | 83013-85-8

• 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: (+)-onoceranoxide
• 英文别名: onoceranoxide；(1R,3R,6S,11S,12R,15R,16S,21S)-1,3,7,7,11,16,20,20-octamethyl-2-oxapentacyclo[13.8.0.03,12.06,11.016,21]tricosane
• CAS: 83013-85-8
• 化学式: C₃₀H₅₂O
• 分子量: 428.742
• InChiKey: WKJQOTFJIQYADY-QPYQYMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1R,3R,6R,8S,11S,12R,15R,16S,21S)-1,3,7,7,11,16,20,20-octamethyl-2-oxapentacyclo[13.8.0.03,12.06,11.016,21]tricosan-8-ol 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (+)-onoceranoxide
  参考文献：
  名称：

  五环金刚烷三萜类化合物的生物启发性合成

  摘要：

  已经实现了五环二十烷三萜的第一化学合成。假定的仿生三环化级联被用于锻造稠合的十氢化萘-/氧杂环丁烷环系统。当从香叶草酰氯和（+）-香紫苏内酯开始时，合成路线以最长的线性顺序以七个步骤进行（+）-cupacinoxepin，并以八个步骤进行（+）-二十二碳酰氧。生物启发的环氧多烯环化得到计算和酶促研究的支持。

  DOI：

  10.1039/c7sc03903d

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。
• 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.
• Bioinspired synthesis of pentacyclic onocerane triterpenoids
  作者：Florian Bartels、Young J. Hong、Daijiro Ueda、Manuela Weber、Tsutomu Sato、Dean J. Tantillo、Mathias Christmann

  DOI：10.1039/c7sc03903d

  日期：——

  The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired

  已经实现了五环二十烷三萜的第一化学合成。假定的仿生三环化级联被用于锻造稠合的十氢化萘-/氧杂环丁烷环系统。当从香叶草酰氯和（+）-香紫苏内酯开始时，合成路线以最长的线性顺序以七个步骤进行（+）-cupacinoxepin，并以八个步骤进行（+）-二十二碳酰氧。生物启发的环氧多烯环化得到计算和酶促研究的支持。