meso-Dimethyl 2,5-dibromoadipate | 53490-47-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: meso-Dimethyl 2,5-dibromoadipate
• 英文别名: dimethyl (2S,5S)-2,5-dibromohexanedioate
• CAS: 53490-47-4
• 化学式: C₈H₁₂Br₂O₄
• 分子量: 331.989
• InChiKey: HVICCJCVLLCDFQ-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2917190090

反应信息

• 作为反应物：
  描述：

  meso-Dimethyl 2,5-dibromoadipate 在 palladium on activated charcoal 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 47.0h， 生成 cis-2,5-dimethyl pyrrolidine-2,5-dicarboxylate
  参考文献：
  名称：

  Prolinyl Phosphoramidates of Nucleotides with Increased Reactivity

  摘要：

  Nucleoside monophosphates (NMPs) are the subunits of RNA. They are incorporated into growing complementary strands when sequences are copied in enzyme‐free reactions using organic leaving groups at the phosphates. Amino acids are rarely considered as leaving groups, but proline can act as a leaving group when N‐linked to NMPs, so that prolinyl NMPs hydrolyze in aqueous buffer at 37 °C, with half‐life times as short as 2.4 h, and they act as monomers in enzyme‐free primer extension. Still, their level of reactivity is insufficient for practical purposes, requiring months for some extensions. Herein we report the synthesis of eight substituted prolinyl AMPs together with seven related compounds and the results of a study of their reactivity. A δ‐carboxy prolinyl NMP was found to be converted with a half‐life time of just 11 min in magnesium‐free buffer, and a δ‐isopropyl prolinyl NMP was shown to react sevenfold faster than its prolinyl counterpart in enzyme‐free genetic copying of RNA. Our results indicate that both anchimeric and steric effects can be employed to increase the reactivity of aminoacidyl nucleotides, i.e. compounds that combine two fundamental classes of biomolecules in one functional entity.

  DOI：

  10.1002/anie.202319958
• 作为产物：
  描述：

  己二酰氯 在 溴 作用下， 反应 2.0h， 生成 meso-Dimethyl 2,5-dibromoadipate
  参考文献：
  名称：

  A reinvestigation and improvement in the synthesis of meso-2,5-dibromoadipates by application of Le Chatelier's principle

  摘要：

  DOI：

  10.1021/jo00296a071

文献信息

• A reinvestigation and improvement in the synthesis of meso-2,5-dibromoadipates by application of Le Chatelier's principle
  作者：H. A. Watson、B. T. O'Neill

  DOI：10.1021/jo00296a071

  日期：1990.4
• Prolinyl Phosphoramidates of Nucleotides with Increased Reactivity
  作者：Adrian Humboldt、Fabian Rami、Franka M. Topp、Dejana Arnold、Daniela Göhringer、Pradeep S. Pallan、Martin Egli、Clemens Richert

  DOI：10.1002/anie.202319958

  日期：2024.4.8

  Nucleoside monophosphates (NMPs) are the subunits of RNA. They are incorporated into growing complementary strands when sequences are copied in enzyme‐free reactions using organic leaving groups at the phosphates. Amino acids are rarely considered as leaving groups, but proline can act as a leaving group when N‐linked to NMPs, so that prolinyl NMPs hydrolyze in aqueous buffer at 37 °C, with half‐life times as short as 2.4 h, and they act as monomers in enzyme‐free primer extension. Still, their level of reactivity is insufficient for practical purposes, requiring months for some extensions. Herein we report the synthesis of eight substituted prolinyl AMPs together with seven related compounds and the results of a study of their reactivity. A δ‐carboxy prolinyl NMP was found to be converted with a half‐life time of just 11 min in magnesium‐free buffer, and a δ‐isopropyl prolinyl NMP was shown to react sevenfold faster than its prolinyl counterpart in enzyme‐free genetic copying of RNA. Our results indicate that both anchimeric and steric effects can be employed to increase the reactivity of aminoacidyl nucleotides, i.e. compounds that combine two fundamental classes of biomolecules in one functional entity.