(2Z,6E,10E)-ethyl 7,11,15-trimethyl-3-diethylphosphoryloxy-6,10,14-trienoate

• 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: (2Z,6E,10E)-ethyl 7,11,15-trimethyl-3-diethylphosphoryloxy-6,10,14-trienoate
• 英文别名: ethyl (2Z,6E,10E)-3-diethoxyphosphoryloxy-7,11,15-trimethylhexadeca-2,6,10,14-tetraenoate
• 化学式: C₂₅H₄₃O₆P
• 分子量: 470.587
• InChiKey: NUGFSECZJBXADK-PRAVLZDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2Z,6E,10E)-ethyl 7,11,15-trimethyl-3-diethylphosphoryloxy-6,10,14-trienoate 在 copper(l) iodide 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 3.0h， 生成 香叶基香叶醇
  参考文献：
  名称：

  Identification of CDP-Archaeol Synthase, a Missing Link of Ether Lipid Biosynthesis in Archaea

  摘要：

  Archaeal membrane lipid composition is distinct from Bacteria and Eukarya, consisting of isoprenoid chains etherified to the glycerol carbons. Biosynthesis of these lipids is poorly understood. Here we identify and characterize the archaeal membrane protein CDP-archaeol synthase (CarS) that catalyzes the transfer of the nucleotide to its specific archaeal lipid substrate, leading to the formation of a CDP-activated precursor (CDP-archaeol) to which polar head groups are attached. The discovery of CarS enabled reconstitution of the entire archaeal lipid biosynthesis pathway in vitro, starting from simple isoprenoid building blocks and using a set of five purified enzymes. The cell free synthetic strategy for archaeal lipids we describe opens opportunity for studies of archaeal lipid biochemistry. Additionally, insights into archaeal lipid biosynthesis reported here allow addressing the evolutionary hypothesis of the lipid divide between Archaea and Bacteria.

  DOI：

  10.1016/j.chembiol.2014.07.022
• 作为产物：
  描述：

  反式,反式-金合欢醇 在 sodium hydride 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.58h， 生成 (2Z,6E,10E)-ethyl 7,11,15-trimethyl-3-diethylphosphoryloxy-6,10,14-trienoate
  参考文献：
  名称：

  Identification of CDP-Archaeol Synthase, a Missing Link of Ether Lipid Biosynthesis in Archaea

  摘要：

  Archaeal membrane lipid composition is distinct from Bacteria and Eukarya, consisting of isoprenoid chains etherified to the glycerol carbons. Biosynthesis of these lipids is poorly understood. Here we identify and characterize the archaeal membrane protein CDP-archaeol synthase (CarS) that catalyzes the transfer of the nucleotide to its specific archaeal lipid substrate, leading to the formation of a CDP-activated precursor (CDP-archaeol) to which polar head groups are attached. The discovery of CarS enabled reconstitution of the entire archaeal lipid biosynthesis pathway in vitro, starting from simple isoprenoid building blocks and using a set of five purified enzymes. The cell free synthetic strategy for archaeal lipids we describe opens opportunity for studies of archaeal lipid biochemistry. Additionally, insights into archaeal lipid biosynthesis reported here allow addressing the evolutionary hypothesis of the lipid divide between Archaea and Bacteria.

  DOI：

  10.1016/j.chembiol.2014.07.022

文献信息

• STEREOSELECTIVE ISOPRENOID CHAIN EXTENSION WITH ACETOACETATE DIANION:
  作者：Jin, Yinghua、Roberts, Frank G.、Coates, Robert M.、Peltier, Hillary M.、Ellman, Jonathan A.

  DOI：10.15227/orgsyn.084.0043

  日期：——
• Identification of CDP-Archaeol Synthase, a Missing Link of Ether Lipid Biosynthesis in Archaea
  作者：Samta Jain、Antonella Caforio、Peter Fodran、Juke S. Lolkema、Adriaan J. Minnaard、Arnold J.M. Driessen

  DOI：10.1016/j.chembiol.2014.07.022

  日期：2014.10

  Archaeal membrane lipid composition is distinct from Bacteria and Eukarya, consisting of isoprenoid chains etherified to the glycerol carbons. Biosynthesis of these lipids is poorly understood. Here we identify and characterize the archaeal membrane protein CDP-archaeol synthase (CarS) that catalyzes the transfer of the nucleotide to its specific archaeal lipid substrate, leading to the formation of a CDP-activated precursor (CDP-archaeol) to which polar head groups are attached. The discovery of CarS enabled reconstitution of the entire archaeal lipid biosynthesis pathway in vitro, starting from simple isoprenoid building blocks and using a set of five purified enzymes. The cell free synthetic strategy for archaeal lipids we describe opens opportunity for studies of archaeal lipid biochemistry. Additionally, insights into archaeal lipid biosynthesis reported here allow addressing the evolutionary hypothesis of the lipid divide between Archaea and Bacteria.