7-desmethylgeranylgeranyl diphosphate | 944579-53-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 7-desmethylgeranylgeranyl diphosphate
• CAS: 944579-53-7
• 化学式: C₁₉H₃₄O₇P₂
• 分子量: 436.422
• InChiKey: MZSDVNTUMYJWHD-PZKHUXIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  113.29
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-desmethylgeranylgeranyl diphosphate 在 wanjudiene synthase from Chryseobacterium wanjuense 作用下， 以 二苯醚 为溶剂， 反应 3.0h， 生成 19-nor-prewanjuelemene
  参考文献：
  名称：

  实验与理论的结合：萜类烃的应对重排和热 E/Z 异构化

  摘要：

  通过实验研究了三种二萜类化合物的热反应，包括 Cope 重排和 E/Z 异构化。此外，还进行了 DFT 计算以解释本研究和文献中相关系统的实验结果。结果表明，只有考虑大多数稳定构象异构体的集合，才能获得准确的计算数据。

  DOI：

  10.1002/ejoc.202400583
• 作为产物：
  描述：

  7-desmethylgeranylgeranyl bromide 在 (Bu₄N)tris(tetrabutylammonium) hydrogen diphosphate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以1.1 mmol的产率得到7-desmethylgeranylgeranyl diphosphate
  参考文献：
  名称：

  Studies on taxadiene synthase: interception of the cyclization cascade at the verticillene stage and rearrangement to phomactatriene

  摘要：

  The cyclization of geranylgeranyl diphosphate ( GGDP) to taxadiene catalyzed by taxadiene synthase has been suggested to proceed in stages, involving a transient bicyclic verticillyl carbocation intermediate, which also has been proposed in the biosynthetic pathway leading to phomactatriene by marine fungi of Phoma sp. On incubation with des-7-methylGGDP, which would be expected to decrease the stability of a carbocation produced by hydride migration, taxadiene synthase produced phomactatrienes as major products. This indicates that the verticillyl carbocation was indeed formed but underwent further skeletal rearrangements, diverging from the usual pathway taken by GGDP en route to taxadiene. Products were identified using GC-MS, one- and two-dimensional NMR, and X-ray crystallography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.029

文献信息

• The Diterpenoid Substrate Analogue 19‐<i>nor</i>‐GGPP Reveals Pronounced Methyl Group Effects in Diterpene Cyclisations
  作者：Kizerbo A. Taizoumbe、Bernd Goldfuss、Jeroen S. Dickschat

  DOI：10.1002/anie.202318375

  日期：2024.2.5

  te (with a methyl group removed) has been synthesised and converted into diterpene analogues with 20 diterpene synthases. In some cases only the desmethyl derivatives of the natural enzyme products were obtained, but with several enzymes a dramatic change in the reactivity was observed. The newly opened reaction paths to compounds with unknown skeletons reveal an intriguing methyl group effect in diterpene

  已合成 19-正-香叶基香叶基二磷酸（除去甲基）并用 20 个二萜合酶将其转化为二萜类似物。在某些情况下，仅获得了天然酶产品的去甲基衍生物，但观察到几种酶的反应性发生显着变化。新开辟的未知骨架化合物的反应路径揭示了二萜生物合成中有趣的甲基效应。