3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl iodide | 1131915-28-0

• 英文名称: 3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl iodide
• 英文别名: tert-butyl N-[3-[3-iodopropyl-(2-nitrophenyl)sulfonylamino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 1131915-28-0
• 化学式: C₃₄H₅₈IN₅O₁₀S
• 分子量: 855.833
• InChiKey: JTMMJVKIUUKSTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  189
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 9.0h， 以1.4 g的产率得到3-[1-(2-nitrobenzenesulfonyl)-5,10,14-tris-Boc-spermine]propanyl iodide
  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