Nα-alloc-Nε-[3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl]-Nε-(2-nitrobenzenesulfonyl)-L-lysine allyl ester | 1131915-31-5

• 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: Nα-alloc-Nε-[3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl]-Nε-(2-nitrobenzenesulfonyl)-L-lysine allyl ester
• 英文别名: prop-2-enyl (2S)-6-[3-[3-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]amino]propyl-(2-nitrophenyl)sulfonylamino]propyl-(2-nitrophenyl)sulfonylamino]-2-(prop-2-enoxycarbonylamino)hexanoate
• CAS: 1131915-31-5
• 化学式: C₅₃H₈₂N₈O₁₈S₂
• 分子量: 1183.41
• InChiKey: SEVCJLWLZVMROG-RWYGWLOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  81
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  345
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  Nα-alloc-Nε-[3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl]-Nε-(2-nitrobenzenesulfonyl)-L-lysine allyl ester 在 四氢吡咯 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以48%的产率得到Nε-[3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl]-Nε-(2-nitrobenzenesulfonyl)-L-lysine
  参考文献：
  名称：

  Synthesis and Applications of Polyamine Amino Acid Residues: Improving the Bioactivity of an Analgesic Neuropeptide, Neurotensin

  摘要：

  Conjugated polyamines are potential carriers for biotherapeutics targeting the central nervous system. We describe an efficient synthesis of a polyamine-based amino acid, lysine-trimethylene(diNo-syl)-spermine(triBoc) with Dde or Fmoc orthogonal protecting groups. This nonnatural amino acid was incorporated into a neurotensin analogue using standard Fmoc-based protocols. The analogue maintained high affinity and agonist potency for neurotensin receptors and exhibited dramatically improved analgesia in mice. Our work provides a basis for use of polyamine amino acids in polypeptides.

  DOI：

  10.1021/jm801481y
• 作为产物：
  描述：

  Alloc-Lys(Ns)-OAll 、 3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl iodide 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以72%的产率得到Nα-alloc-Nε-[3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl]-Nε-(2-nitrobenzenesulfonyl)-L-lysine allyl ester
  参考文献：
  名称：

  Synthesis and Applications of Polyamine Amino Acid Residues: Improving the Bioactivity of an Analgesic Neuropeptide, Neurotensin

  摘要：

  Conjugated polyamines are potential carriers for biotherapeutics targeting the central nervous system. We describe an efficient synthesis of a polyamine-based amino acid, lysine-trimethylene(diNo-syl)-spermine(triBoc) with Dde or Fmoc orthogonal protecting groups. This nonnatural amino acid was incorporated into a neurotensin analogue using standard Fmoc-based protocols. The analogue maintained high affinity and agonist potency for neurotensin receptors and exhibited dramatically improved analgesia in mice. Our work provides a basis for use of polyamine amino acids in polypeptides.

  DOI：

  10.1021/jm801481y

文献信息

• Synthesis and Applications of Polyamine Amino Acid Residues: Improving the Bioactivity of an Analgesic Neuropeptide, Neurotensin
  作者：Liuyin Zhang、Hee-Kyoung Lee、Timothy H. Pruess、H. Steve White、Grzegorz Bulaj

  DOI：10.1021/jm801481y

  日期：2009.3.26

  Conjugated polyamines are potential carriers for biotherapeutics targeting the central nervous system. We describe an efficient synthesis of a polyamine-based amino acid, lysine-trimethylene(diNo-syl)-spermine(triBoc) with Dde or Fmoc orthogonal protecting groups. This nonnatural amino acid was incorporated into a neurotensin analogue using standard Fmoc-based protocols. The analogue maintained high affinity and agonist potency for neurotensin receptors and exhibited dramatically improved analgesia in mice. Our work provides a basis for use of polyamine amino acids in polypeptides.