sn-3-O-(geranylgeranyl)glycerol 1-phosphate

• 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: sn-3-O-(geranylgeranyl)glycerol 1-phosphate
• 英文别名: (S)-3-O-geranylgeranylglyceryl phosphate；[(2S)-2-hydroxy-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoxy]propyl] dihydrogen phosphate
• 化学式: C₂₃H₄₁O₆P
• 分子量: 444.549
• InChiKey: BJLPWUCPFAJINB-UAQSTNRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sn-3-O-(geranylgeranyl)glycerol 1-phosphate 生成 (-)-(R)-1-O-geranylgeranylglycerol
  参考文献：
  名称：

  ZHANG, DONG-LU;DANIELS, LACY;POULTER, C. DALE, J. AMER. CHEM. SOC., 112,(1990) N, C. 1264-1265

  摘要：

  DOI：
• 作为产物：
  描述：

  香叶基香叶醇 在 吡啶 、 2,4,6-三甲基吡啶 、 三甲基溴硅烷 、 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 30.0h， 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

文献信息

• Biosynthesis of archaebacterial ether lipids. Formation of ether linkages by prenyltransferases
  作者：Donglu Zhang、C. Dale Poulter

  DOI：10.1021/ja00057a008

  日期：1993.2

  Biosynthesis of (R)-2,3-di-O-phytanylglycerol (1), the core lipid of the membranes in the strict anaerobe Methanobacterium thermoautotrophicum, was studied in cell-free preparation. Two prenyltransferase activities were separated by ultracentrifugation. The cytosolic fraction contained activity for (S)-3-O-geranylgeranylglyceryl phosphate synthase (CGGP synthase), which catalyzes alkylation of (S)-glyceryl

  在无细胞制备中研究了 (R)-2,3-di-O-phytanylglycerol (1) 的生物合成，这是严格厌氧型嗜热自养甲烷杆菌膜的核心脂质。通过超速离心分离两种异戊二烯基转移酶活性。胞质部分含有 (S)-3-O-香叶基香叶基甘油基磷酸合酶 (CGGP 合酶) 的活性，该酶催化 (S)-甘油基磷酸酯 [(S)-3-OP] 被香叶基香叶基二磷酸 (5-OPP) 烷基化，而颗粒含有 (S)-2,3-O-二香叶基香叶基甘油基磷酸合酶 (DGGGP 合酶) 的活性，该酶催化 (S)-3-O-香叶基香叶基甘油基磷酸酯 [(S)-12-OP] 通过 5-奥普
• ZHANG, DONG-LU;DANIELS, LACY;POULTER, C. DALE, J. AMER. CHEM. SOC., 112,(1990) N, C. 1264-1265
  作者：ZHANG, DONG-LU、DANIELS, LACY、POULTER, C. DALE

  DOI：——

  日期：——
• 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.