di-tert-butyl 9-((4S,7S,10S,13S,16S,19S)-4-benzyl-7,13,19-triisobutyl-10,16-dimethyl-3,6,9,12,15,18,21-heptaoxo-2-oxa-5,8,11,14,17,20-hexaazadocosan-22-yl)-1,5,9-triazacyclododecane-1,5-dicarboxylate | 1374225-27-0

• 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: di-tert-butyl 9-((4S,7S,10S,13S,16S,19S)-4-benzyl-7,13,19-triisobutyl-10,16-dimethyl-3,6,9,12,15,18,21-heptaoxo-2-oxa-5,8,11,14,17,20-hexaazadocosan-22-yl)-1,5,9-triazacyclododecane-1,5-dicarboxylate
• CAS: 1374225-27-0
• 化学式: C₅₅H₉₃N₉O₁₂
• 分子量: 1072.4
• InChiKey: GSSNHYBTBDYEDH-DQFYXGQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  76.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  263.22
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 9-((4S,7S,10S,13S,16S,19S)-4-benzyl-7,13,19-triisobutyl-10,16-dimethyl-3,6,9,12,15,18,21-heptaoxo-2-oxa-5,8,11,14,17,20-hexaazadocosan-22-yl)-1,5,9-triazacyclododecane-1,5-dicarboxylate 在 甲醇 、 乙酰氯 作用下， 反应 12.0h， 以88%的产率得到methyl (2S)-2-[[(2S)-4-methyl-2-[[(2S)-2-[[(2S)-4-methyl-2-[[(2S)-2-[[(2S)-4-methyl-2-[[2-(1,5,9-triazacyclododec-1-yl)acetyl]amino]pentanoyl]amino]propanoyl]amino]pentanoyl]amino]propanoyl]amino]pentanoyl]amino]-3-phenylpropanoate;hydrochloride
  参考文献：
  名称：

  Syntheses of [12]aneN3–oligopeptide conjugates as effective DNA condensation agents

  摘要：

  With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN(3) conjugates 7a-h center dot 3HCl have been designed and synthesized through multi-step amidation reactions. Structure-property study through gel electrophoresis proved that the conjugates containing high hydrophobic ending amino acids exhibited effective condensation ability at concentration of 150-250 mu M, which was further confirmed by dynamic light scattering and atomic force microscopy experiments. EB displacement assay, ionic salt effect, and structure-property relationship in gel electrophoresis indicated that DNA condensation resulted from both the electrostatic interaction of [12]aneN(3) unit and hydrogen-bonding/hydrophobic multi-interaction of oligopeptide moiety in the conjugates with DNA. The reversible condensation process and their low cytotoxicity suggest that the new condensing agents are potential for the development of non-viral vectors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.022
• 作为产物：
  描述：

  (2S)-((2'S)-tert-butoxycarbonylamino-4-methylpentanoylamino)propionic acid 在 盐酸 、 lithium hydroxide monohydrate 、 水 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 di-tert-butyl 9-((4S,7S,10S,13S,16S,19S)-4-benzyl-7,13,19-triisobutyl-10,16-dimethyl-3,6,9,12,15,18,21-heptaoxo-2-oxa-5,8,11,14,17,20-hexaazadocosan-22-yl)-1,5,9-triazacyclododecane-1,5-dicarboxylate
  参考文献：
  名称：

  Syntheses of [12]aneN3–oligopeptide conjugates as effective DNA condensation agents

  摘要：

  With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN(3) conjugates 7a-h center dot 3HCl have been designed and synthesized through multi-step amidation reactions. Structure-property study through gel electrophoresis proved that the conjugates containing high hydrophobic ending amino acids exhibited effective condensation ability at concentration of 150-250 mu M, which was further confirmed by dynamic light scattering and atomic force microscopy experiments. EB displacement assay, ionic salt effect, and structure-property relationship in gel electrophoresis indicated that DNA condensation resulted from both the electrostatic interaction of [12]aneN(3) unit and hydrogen-bonding/hydrophobic multi-interaction of oligopeptide moiety in the conjugates with DNA. The reversible condensation process and their low cytotoxicity suggest that the new condensing agents are potential for the development of non-viral vectors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.022