p-Nitrobenzyl monoester of glutaric acid | 117679-89-7

• 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: p-Nitrobenzyl monoester of glutaric acid
• 英文别名: Mono(4-nitrobenzyl) glutarate；mono-p-nitrobenzyl glutarate；5-[(4-Nitrophenyl)methoxy]-5-oxopentanoic acid
• CAS: 117679-89-7
• 化学式: C₁₂H₁₃NO₆
• 分子量: 267.238
• InChiKey: WZGMJALOYSCCPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 p-Nitrobenzyl monoester of glutaric acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到Succinimido ester of p-nitrobenzyl glutarate
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013
• 作为产物：
  描述：

  戊二酸酐 、 对硝基苯甲醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以98%的产率得到p-Nitrobenzyl monoester of glutaric acid
  参考文献：
  名称：

  对硝基苄基酯保护基的抗体催化去除：广泛的底物特异性的分子基础。

  摘要：

  已经产生了用于去除对硝基苄基酯保护基的抗体催化剂，以适应各种各样的底物。针对对硝基苄基膦酸酯1引发的抗体7B9催化了具有几乎相同的Km和kcat值的未取代的β-和γ-取代的戊二酸对硝基苄基单酯的水解。另外，7B9表现出对α-取代基的底物耐受性，并接受Leu，Norleu和Phe的对硝基苄基酯。为了定义广泛的底物耐受性的分子基础，我们已经克隆并测序了抗体，并构建了活性位点-半抗原复合物的模型。该模型显示抗原结合位点的相对较浅的口袋可以容纳对硝基苄基部分，这与观察到的底物特异性一致。因此，在抗体催化的反应中，底物的α，β和γ取代基应位于结合位点之外，并被抗体识别所忽略。针对结构相似的半抗原膦酸酯引发的7B9与抗体D2.3的结构比较表明，连接体部分在半抗原设计中具有重要意义，从而使抗体催化剂具有广泛的底物特异性。这些研究为产生催化抗体提供了新的策略，该催化抗体可广泛应用于有机合成化学的实际应用。

  DOI：

  10.1002/(sici)1521-3765(20000502)6:9<1656::aid-chem1656>3.3.co;2-1

文献信息

• NOVEL BONE-SEEKING ESTROGEN DERIVATIVE
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0827951A1

  公开（公告）日：1998-03-11

  A novel estrogen derivative represented by the formula: is useful for treating or preventing diseases caused by estrogen deficiency.

  一种由式表示的新型雌激素衍生物： 可用于治疗或预防由雌激素缺乏引起的疾病。
• US5962438A
  申请人：——

  公开号：US5962438A

  公开（公告）日：1999-10-05
• Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs
  作者：Sushil K. Sharma、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00122a013

  日期：1989.2

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.
• Antibody-Catalyzed Removal of the p-Nitrobenzyl Ester Protecting Group: The Molecular Basis of Broad Substrate Specificity
  作者：Shinwa Kurihara、Takeshi Tsumuraya、Kayo Suzuki、Masataka Kuroda、Lidong Liu、Yumiko Takaoka、Ikuo Fujii

  DOI：10.1002/(sici)1521-3765(20000502)6:9<1656::aid-chem1656>3.3.co;2-1

  日期：2000.5.2

  Antibody catalysts for the removal of the p-nitrobenzyl ester protecting group have been generated to accommodate a broad range of substrates. Antibody 7B9, which was elicited against p-nitrobenzyl phosphonate 1, catalyzed the hydrolyses of p-nitrobenzyl monoesters of nonsubstituted, and beta- and gamma-substituted glutaric acids with almost identical Km and kcat values. In addition, 7B9 displayed

  已经产生了用于去除对硝基苄基酯保护基的抗体催化剂，以适应各种各样的底物。针对对硝基苄基膦酸酯1引发的抗体7B9催化了具有几乎相同的Km和kcat值的未取代的β-和γ-取代的戊二酸对硝基苄基单酯的水解。另外，7B9表现出对α-取代基的底物耐受性，并接受Leu，Norleu和Phe的对硝基苄基酯。为了定义广泛的底物耐受性的分子基础，我们已经克隆并测序了抗体，并构建了活性位点-半抗原复合物的模型。该模型显示抗原结合位点的相对较浅的口袋可以容纳对硝基苄基部分，这与观察到的底物特异性一致。因此，在抗体催化的反应中，底物的α，β和γ取代基应位于结合位点之外，并被抗体识别所忽略。针对结构相似的半抗原膦酸酯引发的7B9与抗体D2.3的结构比较表明，连接体部分在半抗原设计中具有重要意义，从而使抗体催化剂具有广泛的底物特异性。这些研究为产生催化抗体提供了新的策略，该催化抗体可广泛应用于有机合成化学的实际应用。