[(2S)-2-hydroxy-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]propyl] dimethyl phosphate | 880168-47-8

• 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: [(2S)-2-hydroxy-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]propyl] dimethyl phosphate
• CAS: 880168-47-8
• 化学式: C₂₅H₄₅O₆P
• 分子量: 472.602
• InChiKey: CQSJDIQGRQLHKH-ZJAFRZKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S)-2-hydroxy-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]propyl] dimethyl phosphate 在 2,4,6-三甲基吡啶 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 sn-3-O-(geranylgeranyl)glycerol 1-phosphate
  参考文献：
  名称：

  Total Synthesis of Geranylgeranylglyceryl Phosphate Enantiomers:  Substrates for Characterization of 2,3-O-Digeranylgeranylglyceryl Phosphate Synthase

  摘要：

  To determine the entantioselectivity of (S)-2,3-di-O-geranylgeranylglyceryl phosphate synthase (DGGGPS) from the thermoacidophilic archaeon Sulfolobus solfataricus, we developed an efficient enantioselective route to the enantiomeric geranylgeranylglyceryl phosphates (R)-GGGP and (S)-GGGP. Previous routes to these substrates involved enzymatic conversions due to the lability of the polyprenyl chains toward common phosphorylation reaction conditions. The synthesis described herein employs a mild trimethyl phosphite/carbon tetrabromide oxidative phosphorylation to circumvent this problem. In contrast to previous results suggesting that only (S)-GGGP can act as the prenyl acceptor substrate, both (R)-GGGP and (S)-GGGP were found to be substrates for DGGGPS.

  DOI：

  10.1021/ol0530878
• 作为产物：
  描述：

  香叶基香叶醇 在 吡啶 、 四溴化碳 、 potassium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 [(2S)-2-hydroxy-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]propyl] dimethyl phosphate
  参考文献：
  名称：

  Total Synthesis of Geranylgeranylglyceryl Phosphate Enantiomers:  Substrates for Characterization of 2,3-O-Digeranylgeranylglyceryl Phosphate Synthase

  摘要：

  To determine the entantioselectivity of (S)-2,3-di-O-geranylgeranylglyceryl phosphate synthase (DGGGPS) from the thermoacidophilic archaeon Sulfolobus solfataricus, we developed an efficient enantioselective route to the enantiomeric geranylgeranylglyceryl phosphates (R)-GGGP and (S)-GGGP. Previous routes to these substrates involved enzymatic conversions due to the lability of the polyprenyl chains toward common phosphorylation reaction conditions. The synthesis described herein employs a mild trimethyl phosphite/carbon tetrabromide oxidative phosphorylation to circumvent this problem. In contrast to previous results suggesting that only (S)-GGGP can act as the prenyl acceptor substrate, both (R)-GGGP and (S)-GGGP were found to be substrates for DGGGPS.

  DOI：

  10.1021/ol0530878

文献信息

• Total Synthesis of Geranylgeranylglyceryl Phosphate Enantiomers:  Substrates for Characterization of 2,3-<i>O</i>-Digeranylgeranylglyceryl Phosphate Synthase
  作者：Honglu Zhang、Kyohei Shibuya、Hisashi Hemmi、Tokuzo Nishino、Glenn D. Prestwich

  DOI：10.1021/ol0530878

  日期：2006.3.2

  To determine the entantioselectivity of (S)-2,3-di-O-geranylgeranylglyceryl phosphate synthase (DGGGPS) from the thermoacidophilic archaeon Sulfolobus solfataricus, we developed an efficient enantioselective route to the enantiomeric geranylgeranylglyceryl phosphates (R)-GGGP and (S)-GGGP. Previous routes to these substrates involved enzymatic conversions due to the lability of the polyprenyl chains toward common phosphorylation reaction conditions. The synthesis described herein employs a mild trimethyl phosphite/carbon tetrabromide oxidative phosphorylation to circumvent this problem. In contrast to previous results suggesting that only (S)-GGGP can act as the prenyl acceptor substrate, both (R)-GGGP and (S)-GGGP were found to be substrates for DGGGPS.