1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-sn-glycerol | 888959-48-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-sn-glycerol
• 英文别名: [(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypropyl] 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 888959-48-6
• 化学式: C₂₀H₄₁NO₆Si
• 分子量: 419.634
• InChiKey: LGQOQZGEEAIPAG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-sn-glycerol 在 palladium on activated charcoal 四氮唑 、 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -40.0~20.0 ℃ 、344.74 kPa 条件下， 反应 7.5h， 生成 [(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[2-[3-[2-[2-[2-[2-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]ethoxy-hydroxyphosphoryl]oxypropyl] 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  Fluorogenic Phospholipid Substrate to Detect Lysophospholipase D/Autotaxin Activity

  摘要：

  Lysophospholipase D (lysoPLD), also known as autotaxin (ATX), is an important source of the potent mitogen lysophosphatidic acid (LPA). Two fluorogenic substrate analogues for lysoPLD were synthesized in nine steps from (S)-PMB-glycerol. The substrates (FS-2 and FS-3) show significant increases in fluorescence when treated with recombinant ATX and have potential applications in screening for this emerging drug target.

  DOI：

  10.1021/ol060414i
• 作为产物：
  描述：

  叔丁氧羰酰基6-氨基己酸 在 咪唑 、 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-sn-glycerol
  参考文献：
  名称：

  Fluorogenic Phospholipid Substrate to Detect Lysophospholipase D/Autotaxin Activity

  摘要：

  Lysophospholipase D (lysoPLD), also known as autotaxin (ATX), is an important source of the potent mitogen lysophosphatidic acid (LPA). Two fluorogenic substrate analogues for lysoPLD were synthesized in nine steps from (S)-PMB-glycerol. The substrates (FS-2 and FS-3) show significant increases in fluorescence when treated with recombinant ATX and have potential applications in screening for this emerging drug target.

  DOI：

  10.1021/ol060414i

文献信息

• Fluorogenic Phospholipid Substrate to Detect Lysophospholipase D/Autotaxin Activity
  作者：Colin G. Ferguson、Cleve S. Bigman、Robyn D. Richardson、Laurens A. van Meeteren、Wouter H. Moolenaar、Glenn D. Prestwich

  DOI：10.1021/ol060414i

  日期：2006.5.1

  Lysophospholipase D (lysoPLD), also known as autotaxin (ATX), is an important source of the potent mitogen lysophosphatidic acid (LPA). Two fluorogenic substrate analogues for lysoPLD were synthesized in nine steps from (S)-PMB-glycerol. The substrates (FS-2 and FS-3) show significant increases in fluorescence when treated with recombinant ATX and have potential applications in screening for this emerging drug target.