2,6,10,14,19,23,27-heptamethyl-2,6E,10E,14E,18E,22E,26-octacosaheptaene | 126812-44-0

• 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: 2,6,10,14,19,23,27-heptamethyl-2,6E,10E,14E,18E,22E,26-octacosaheptaene
• 英文别名: (6E,10E,14E,18E,22E)-2,6,10,14,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaene
• CAS: 126812-44-0
• 化学式: C₃₅H₅₈
• 分子量: 478.846
• InChiKey: KGAOUWKDZSNZBB-JWNDACAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6,10,14,19,23,27-heptamethyl-2,6E,10E,14E,18E,22E,26-octacosaheptaene 在 recombinant A_. acidocaldarius squalene:hopene cyclase 、 sodium citrate 、 Triton X-100 作用下， 反应 16.0h， 以10%的产率得到(1R,2R,5S,10S,11R,14R,15S,18S,19R,22S,23S)-1,2,6,6,10,15,22-heptamethyl-19-prop-1-en-2-ylhexacyclo[12.11.0.02,11.05,10.015,23.018,22]pentacosane
  参考文献：
  名称：

  Enzymatic Formation of an Unnatural Hexacyclic C₃₅ Polyprenoid by Bacterial Squalene Cyclase

  摘要：

  A C35 polyprene in which a farnesyl C15 unit is connected in a head-to-head fashion to a geranylgeranyl C20 unit was enzymatically converted to an unnatural hexacyclic polyprenoid by squalene:hopene cyclase from Alicyclobacillus acidocaldarius. This is the first demonstration of the remarkable ability of the squalene cyclizing enzyme to perform construction of unnatural hexacyclic skeleton. The cyclization of the C35 polyprene was initiated by a proton attack on the terminal double bond of the C15 unit and proceeded without rearrangement of carbon and hydrogen. The substrate should be folded in chair-chair-chair-chair-boat-boat conformation to achieve the stereochemistry of the cyclization product.

  DOI：

  10.1021/ja020973u
• 作为产物：
  描述：

  2,3环氧角鲨烯 在 copper(l) iodide 、 氯化亚砜 、 aluminum isopropoxide 、 magnesium 作用下， 以 甲苯 为溶剂， 反应 12.33h， 生成 2,6,10,14,19,23,27-heptamethyl-2,6E,10E,14E,18E,22E,26-octacosaheptaene
  参考文献：
  名称：

  Synthesis of E-C5-homolog of squalene

  摘要：

  DOI：

  10.1007/bf00962117

文献信息

• Synthesis of E-C5-homolog of squalene
  作者：A. B. Veselovskii、T. M. Filippova、A. M. Moiseenkov

  DOI：10.1007/bf00962117

  日期：1989.10
• Enzymatic Formation of an Unnatural Hexacyclic C₃₅ Polyprenoid by Bacterial Squalene Cyclase
  作者：Ikuro Abe、Hideya Tanaka、Hiroshi Noguchi

  DOI：10.1021/ja020973u

  日期：2002.12.1

  A C35 polyprene in which a farnesyl C15 unit is connected in a head-to-head fashion to a geranylgeranyl C20 unit was enzymatically converted to an unnatural hexacyclic polyprenoid by squalene:hopene cyclase from Alicyclobacillus acidocaldarius. This is the first demonstration of the remarkable ability of the squalene cyclizing enzyme to perform construction of unnatural hexacyclic skeleton. The cyclization of the C35 polyprene was initiated by a proton attack on the terminal double bond of the C15 unit and proceeded without rearrangement of carbon and hydrogen. The substrate should be folded in chair-chair-chair-chair-boat-boat conformation to achieve the stereochemistry of the cyclization product.