(2E,6E,10E)-1,1-dideuterio-1-[(2S)-2-[(2E,6E,10E)-1,1-dideuterio-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]-3-[dimethoxy(oxido)phosphaniumyl]oxypropoxy]-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene | 593248-15-8

• 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: (2E,6E,10E)-1,1-dideuterio-1-[(2S)-2-[(2E,6E,10E)-1,1-dideuterio-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]-3-[dimethoxy(oxido)phosphaniumyl]oxypropoxy]-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene
• CAS: 593248-15-8
• 化学式: C₄₅H₇₇O₆P
• 分子量: 749.045
• InChiKey: GPDVJHHLCMDGOO-LTDAPQCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  52
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,6E,10E)-1,1-dideuterio-1-[(2S)-2-[(2E,6E,10E)-1,1-dideuterio-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]-3-[dimethoxy(oxido)phosphaniumyl]oxypropoxy]-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene 在 二氧化碳 、 Methanothermobacter thermautotrophicus JCM 10044^T 、 氢气 作用下， 反应 120.0h， 生成 2,3-bis-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecan-1-yl]-sn-glycerol 、 caldarchaeol
  参考文献：
  名称：

  Importance of the isopropylidene terminal of geranylgeranyl group for the formation of tetraether lipid in methanogenic archaea

  摘要：

  Labeling experiments using several deuterated lipids were pursued to study the biosynthesis of macrocyclic isoprenoidal lipids of thermophilic methanogenic archaea, Methanothermobacter thermautotrophicus. The isopropylidene terminal of geranylgeranyl group of monomeric precursor appeared to be important for the C-C bond formation at the hydrophobic end in the macrocyclic lipids. A mechanism involving a radical trigger at the allylic methyl group is proposed for this C-C bond formation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00627-0
• 作为产物：
  描述：

  methyl (E,E,E)-geranylgeranoate 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 lithium aluminium deuteride 、 二甲基硫 、 sodium hydride 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (2E,6E,10E)-1,1-dideuterio-1-[(2S)-2-[(2E,6E,10E)-1,1-dideuterio-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]-3-[dimethoxy(oxido)phosphaniumyl]oxypropoxy]-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene
  参考文献：
  名称：

  Importance of the isopropylidene terminal of geranylgeranyl group for the formation of tetraether lipid in methanogenic archaea

  摘要：

  Labeling experiments using several deuterated lipids were pursued to study the biosynthesis of macrocyclic isoprenoidal lipids of thermophilic methanogenic archaea, Methanothermobacter thermautotrophicus. The isopropylidene terminal of geranylgeranyl group of monomeric precursor appeared to be important for the C-C bond formation at the hydrophobic end in the macrocyclic lipids. A mechanism involving a radical trigger at the allylic methyl group is proposed for this C-C bond formation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00627-0

文献信息

• Importance of the isopropylidene terminal of geranylgeranyl group for the formation of tetraether lipid in methanogenic archaea
  作者：Tadashi Eguchi、Yuji Nishimura、Katsumi Kakinuma

  DOI：10.1016/s0040-4039(03)00627-0

  日期：2003.4

  Labeling experiments using several deuterated lipids were pursued to study the biosynthesis of macrocyclic isoprenoidal lipids of thermophilic methanogenic archaea, Methanothermobacter thermautotrophicus. The isopropylidene terminal of geranylgeranyl group of monomeric precursor appeared to be important for the C-C bond formation at the hydrophobic end in the macrocyclic lipids. A mechanism involving a radical trigger at the allylic methyl group is proposed for this C-C bond formation. (C) 2003 Elsevier Science Ltd. All rights reserved.