bis(tert-butyl) 3,6-bis[(tert-butoxycarbonyl)methyl]-9-(o-nitrobenzenesulfonyl)-3,6,9-triazaundecanedioate | 1310940-14-7

• 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: bis(tert-butyl) 3,6-bis[(tert-butoxycarbonyl)methyl]-9-(o-nitrobenzenesulfonyl)-3,6,9-triazaundecanedioate
• 英文别名: Tert-butyl 2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-[2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-(2-nitrophenyl)sulfonylamino]ethyl]amino]acetate
• CAS: 1310940-14-7
• 化学式: C₃₄H₅₆N₄O₁₂S
• 分子量: 744.904
• InChiKey: NSPIDPKFRHWDPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  51
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  bis(tert-butyl) 3,6-bis[(tert-butoxycarbonyl)methyl]-9-(o-nitrobenzenesulfonyl)-3,6,9-triazaundecanedioate 在 巯基乙酸 、 lithium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以77%的产率得到bis(tert-butyl) 3,6-bis[(tert-butoxycarbonyl)methyl]-3,6,9-triazaundecanedioate
  参考文献：
  名称：

  Concise site-specific synthesis of DTPA–peptide conjugates: Application to imaging probes for the chemokine receptor CXCR4

  摘要：

  Diethylenetriaminepentaacetic acid (DTPA) is a useful chelating agent for radionuclides such as (68)Ga, (99m)Tc and (111)In, which are applicable to nuclear medicine imaging. In this study, we established a facile synthetic protocol for the production of mono-DTPA-conjugated peptide probes. A novel monoreactive DTPA precursor reagent was synthesized in two steps using the chemistry of the o-nitrobenzenesulfonyl (Ns) protecting group, and under mild conditions this DTPA precursor was incorporated onto an N(epsilon)-bromoacetylated Lys of a protected peptide resin. The site-specific DTPA conjugation was facilitated by using a highly acid-labile 4-methyltrityl (Mtt) protecting group for the target site of the bioactive peptide during the solid-phase synthesis. A combination of both techniques yielded peptides with disulfide bonds, such as octreotide and polyphemusin II-derived CXCR4 antagonists. DTPA-peptide conjugates were purified in a single step following cleavage from the resin and disulfide bond formation. This site-specific on-resin construction strategy was used for the design and synthesis of a novel In-DTPA-labeled CXCR4 antagonist, which exhibited highly potent inhibitory activity against SDF-1-CXCR4 binding. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.059
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.81 g的产率得到bis(tert-butyl) 3,6-bis[(tert-butoxycarbonyl)methyl]-9-(o-nitrobenzenesulfonyl)-3,6,9-triazaundecanedioate
  参考文献：
  名称：

  Concise site-specific synthesis of DTPA–peptide conjugates: Application to imaging probes for the chemokine receptor CXCR4

  摘要：

  Diethylenetriaminepentaacetic acid (DTPA) is a useful chelating agent for radionuclides such as (68)Ga, (99m)Tc and (111)In, which are applicable to nuclear medicine imaging. In this study, we established a facile synthetic protocol for the production of mono-DTPA-conjugated peptide probes. A novel monoreactive DTPA precursor reagent was synthesized in two steps using the chemistry of the o-nitrobenzenesulfonyl (Ns) protecting group, and under mild conditions this DTPA precursor was incorporated onto an N(epsilon)-bromoacetylated Lys of a protected peptide resin. The site-specific DTPA conjugation was facilitated by using a highly acid-labile 4-methyltrityl (Mtt) protecting group for the target site of the bioactive peptide during the solid-phase synthesis. A combination of both techniques yielded peptides with disulfide bonds, such as octreotide and polyphemusin II-derived CXCR4 antagonists. DTPA-peptide conjugates were purified in a single step following cleavage from the resin and disulfide bond formation. This site-specific on-resin construction strategy was used for the design and synthesis of a novel In-DTPA-labeled CXCR4 antagonist, which exhibited highly potent inhibitory activity against SDF-1-CXCR4 binding. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.059