3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanol | 1131915-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanol
• 英文别名: tert-butyl N-[3-[3-hydroxypropyl-(2-nitrophenyl)sulfonylamino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 1131915-25-7
• 化学式: C₃₄H₅₉N₅O₁₁S
• 分子量: 745.935
• InChiKey: LGDIIPHALLIZRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  51
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  209
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanol 、 甲基磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  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：

  tert-butyl (4-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)butyl)(3-(2-nitrophenylsulfonamido)propyl)carbamate 、 3-溴-1-丙醇 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以1.66 g的产率得到3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanol
  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.