(2S)-N-[(2S)-1-[[(2S)-1-[3-[2-[2-[3-[[2-[3-[2-[2-[3-[[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-formamidohexanamide | 1233970-48-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-N-[(2S)-1-[[(2S)-1-[3-[2-[2-[3-[[2-[3-[2-[2-[3-[[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-formamidohexanamide
• CAS: 1233970-48-3
• 化学式: C₆₀H₉₉N₉O₁₇
• 分子量: 1218.5
• InChiKey: BECUBMIAESDXAF-HYGNTPKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  86
• 可旋转键数：
  58
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  342
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (2S)-N-[(2S)-1-[[(2S)-1-[3-[2-[2-[3-[[2-[3-[2-[2-[3-[[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-formamidohexanamide 、 N-Boc-N'-(2-methoxy-3,4-dioxo-1-cyclobuten-1-yl)-4,7,10-trioxa-1,13-tridecane-diamine 在 三乙胺 、 三异丙基硅烷 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 以61%的产率得到(2S)-N-[(2S)-1-[[(2S)-1-[3-[2-[2-[3-[[2-[3-[2-[2-[3-[[2-[3-[2-[2-[3-[[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-formamidohexanamide
  参考文献：
  名称：

  Unexpected Enhancement in Biological Activity of a GPCR Ligand Induced by an Oligoethylene Glycol Substituent

  摘要：

  Polyethylene glycol (PEG) is widely used, and many biologically active molecules are modified with oligoethylene glycol substituents to enhance their half-lives in circulation. The pervasive use of PEG substituents is partly due to their presumed inertness. Our investigation of formyl peptide receptor (FPR)-mediated chemotaxis reveals that oligoethylene glycol substitution can enhance the ability of the peptide chemoattractant N-formyl-methionine-leucine-phenylalanine (fMLF) to activate signal transduction through FPR, a transmembrane G-protein-coupled receptor.

  DOI：

  10.1021/ja102640c
• 作为产物：
  描述：

  (2S)-N-[(2S)-1-[[(2S)-1-[3-[2-[2-[3-[[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-formamidohexanamide 、 N-Boc-N'-(2-methoxy-3,4-dioxo-1-cyclobuten-1-yl)-4,7,10-trioxa-1,13-tridecane-diamine 在 三乙胺 、 三异丙基硅烷 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 以70%的产率得到(2S)-N-[(2S)-1-[[(2S)-1-[3-[2-[2-[3-[[2-[3-[2-[2-[3-[[2-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-3,4-dioxocyclobuten-1-yl]amino]propoxy]ethoxy]ethoxy]propylamino]-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-formamidohexanamide
  参考文献：
  名称：

  Unexpected Enhancement in Biological Activity of a GPCR Ligand Induced by an Oligoethylene Glycol Substituent

  摘要：

  Polyethylene glycol (PEG) is widely used, and many biologically active molecules are modified with oligoethylene glycol substituents to enhance their half-lives in circulation. The pervasive use of PEG substituents is partly due to their presumed inertness. Our investigation of formyl peptide receptor (FPR)-mediated chemotaxis reveals that oligoethylene glycol substitution can enhance the ability of the peptide chemoattractant N-formyl-methionine-leucine-phenylalanine (fMLF) to activate signal transduction through FPR, a transmembrane G-protein-coupled receptor.

  DOI：

  10.1021/ja102640c

文献信息

• Unexpected Enhancement in Biological Activity of a GPCR Ligand Induced by an Oligoethylene Glycol Substituent
  作者：Chutima Jiarpinitnun、Laura L. Kiessling

  DOI：10.1021/ja102640c

  日期：2010.7.7

  Polyethylene glycol (PEG) is widely used, and many biologically active molecules are modified with oligoethylene glycol substituents to enhance their half-lives in circulation. The pervasive use of PEG substituents is partly due to their presumed inertness. Our investigation of formyl peptide receptor (FPR)-mediated chemotaxis reveals that oligoethylene glycol substitution can enhance the ability of the peptide chemoattractant N-formyl-methionine-leucine-phenylalanine (fMLF) to activate signal transduction through FPR, a transmembrane G-protein-coupled receptor.