Acetic acid (E)-(R)-1-((S)-2-{(2-cyano-ethoxy)-[4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butoxy]-phosphoryloxy}-1-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-ethyl)-hexadec-2-enyl ester | 192070-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: Acetic acid (E)-(R)-1-((S)-2-{(2-cyano-ethoxy)-[4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butoxy]-phosphoryloxy}-1-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-ethyl)-hexadec-2-enyl ester
• CAS: 192070-04-5
• 化学式: C₅₅H₈₈N₇O₁₁PS₂
• 分子量: 1118.45
• InChiKey: FNVJCMBONRBVOP-NENNEAFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.11
• 重原子数：
  76.0
• 可旋转键数：
  42.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  243.59
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (E)-(R)-1-((S)-2-{(2-cyano-ethoxy)-[4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butoxy]-phosphoryloxy}-1-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-ethyl)-hexadec-2-enyl ester 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到Phosphoric acid 2-cyano-ethyl ester 4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butyl ester (E)-(2S,3R)-3-hydroxy-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-octadec-4-enyl ester
  参考文献：
  名称：

  Synthesis of novel fluorescently labeled sphingomyelin derivatives useful for sphingomyelinase assay

  摘要：

  Substrates for the sphingomyelinase enzyme class have been prepared, which contain a fluorescent tag and a biotin moiety. These molecules are useful for development of rapid high throughput assays for sphingomyelinase activity. It was observed that retaining the choline ammonium group (as found in the native sphingomyelinase substrate) in synthetic substrates was critical to retain high cleavage rate by the enzyme. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00184-4
• 作为产物：
  描述：

  Acetic acid (E)-(R)-1-((S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-ethyl)-hexadec-2-enyl ester 在 四氮唑 、 叔丁基过氧化氢 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 Acetic acid (E)-(R)-1-((S)-2-{(2-cyano-ethoxy)-[4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butoxy]-phosphoryloxy}-1-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-ethyl)-hexadec-2-enyl ester
  参考文献：
  名称：

  Synthesis of novel fluorescently labeled sphingomyelin derivatives useful for sphingomyelinase assay

  摘要：

  Substrates for the sphingomyelinase enzyme class have been prepared, which contain a fluorescent tag and a biotin moiety. These molecules are useful for development of rapid high throughput assays for sphingomyelinase activity. It was observed that retaining the choline ammonium group (as found in the native sphingomyelinase substrate) in synthetic substrates was critical to retain high cleavage rate by the enzyme. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00184-4