(2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]hexanoic acid | 1312887-03-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]hexanoic acid
• CAS: 1312887-03-8
• 化学式: C₄₄H₆₉N₉O₂₆P₂S
• 分子量: 1234.09
• InChiKey: VTZQJNGFWMTNGK-PMRZBUGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.8
• 重原子数：
  82
• 可旋转键数：
  32
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  547
• 氢给体数：
  16
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]hexanoic acid 在 盐酸 、 水 作用下， 反应 0.17h， 以81%的产率得到
  参考文献：
  名称：

  Synthesis of biotinylated muramyl tripeptides with NOD2-stimulating activity

  摘要：

  Muramyl di- and tri-peptides are putative activators of the innate immune system through stimulation of the NOD2 receptor. To provide tools for the clarification of the mechanism of this activation we isolated different UDP-muramyl tripeptides (Lys- and DAP-type) from bacteria and used them to synthesize biotinylated derivatives. All biotinylated compounds retained their ability to activate NOD2 in a cell-based test system and are therefore suitable for binding studies aimed at identifying the appropriate pattern recognition receptor(s). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.005
• 作为产物：
  描述：

  磺基琥珀生物素 、 UDP-MurNAc-L-Ala-D-Glu-L-Lys 反应 1.0h， 以71%的产率得到(2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[[(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]hexanoic acid
  参考文献：
  名称：

  Synthesis of biotinylated muramyl tripeptides with NOD2-stimulating activity

  摘要：

  Muramyl di- and tri-peptides are putative activators of the innate immune system through stimulation of the NOD2 receptor. To provide tools for the clarification of the mechanism of this activation we isolated different UDP-muramyl tripeptides (Lys- and DAP-type) from bacteria and used them to synthesize biotinylated derivatives. All biotinylated compounds retained their ability to activate NOD2 in a cell-based test system and are therefore suitable for binding studies aimed at identifying the appropriate pattern recognition receptor(s). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.005

文献信息

• Synthesis of biotinylated muramyl tripeptides with NOD2-stimulating activity
  作者：Nicolas Gisch、Birte Buske、Holger Heine、Buko Lindner、Ulrich Zähringer

  DOI：10.1016/j.bmcl.2011.04.005

  日期：2011.6

  Muramyl di- and tri-peptides are putative activators of the innate immune system through stimulation of the NOD2 receptor. To provide tools for the clarification of the mechanism of this activation we isolated different UDP-muramyl tripeptides (Lys- and DAP-type) from bacteria and used them to synthesize biotinylated derivatives. All biotinylated compounds retained their ability to activate NOD2 in a cell-based test system and are therefore suitable for binding studies aimed at identifying the appropriate pattern recognition receptor(s). (C) 2011 Elsevier Ltd. All rights reserved.