6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide
• 英文别名: (3aS,4S,6aR)-hexahydro-N-[6-[[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]amino]-6-oxohexyl]-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide；6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexanamide
• 化学式: C₃₄H₆₂N₄O₅S
• 分子量: 638.956
• InChiKey: AWBCMSFWIASOLO-MDSNSZKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  44
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide 在 吡啶 、 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 8.33h， 生成 Acetic acid (E)-(R)-1-((S)-2-{(2-cyano-ethoxy)-[6-(7-nitro-benzo[1,2,5]oxadiazol-4-ylamino)-hexyloxy]-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

文献信息

• Synthesis of novel fluorescently labeled sphingomyelin derivatives useful for sphingomyelinase assay
  作者：John J. Gaudino、Kirsten Bjergarde、Po-Ying Chan-Hui、Clifford D. Wright、David S. Thomson

  DOI：10.1016/s0960-894x(97)00184-4

  日期：1997.5

  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.