N-{3-[tert-Butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-propyl}-succinamic acid ethyl ester | 508234-81-9

• 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: N-{3-[tert-Butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-propyl}-succinamic acid ethyl ester
• 英文别名: 3-{3-[BOC-(2-BOC-Aminoethyl)-amino]-propylcarbamoyl}-propionic acid ethyl ester
• CAS: 508234-81-9
• 化学式: C₂₁H₃₉N₃O₇
• 分子量: 445.557
• InChiKey: SXPRUOCLEOEKFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-{3-[tert-Butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-propyl}-succinamic acid ethyl ester 在 sodium hydroxide 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  A ribozyme with michaelase activity

  摘要：

  The ability to generate RNA molecules that can catalyze complex organic transformations not only facilitates the reconstruction and plausibility of possible prebiotic reaction pathways but is also crucial for elucidating the potential of the application of RNA catalysts in organic syntheses. Iterative RNA selection previously identified a ribozyme that catalyzes the Michael addition of a cysteine thiol to an alpha,beta-unsaturated amide. This reaction is chemically similar to the rate limiting step of the thymidylate synthase reaction, which is the corresponding reaction of a cysteine thiol to the double-bond of the uracil nucleobase. Here we provide a detailed description of the synthesis of the ribozyme substrates and the substrate oligonucleotides used for its characterization and the investigation of the background reaction. We also describe the further characterization of the ribozyme with respect to substrate specificity. We show that the thiol group of the cysteine nucleophile is essential for the reaction to proceed. When substituted for a thiomethyl group, no reaction takes place. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00311-5
• 作为产物：
  描述：

  tert-butyl N-[2-(2-cyanoethylamino)ethyl]carbamate 在 镍 氢氧化钾 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、300.0 kPa 条件下， 反应 20.0h， 生成 N-{3-[tert-Butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-propyl}-succinamic acid ethyl ester
  参考文献：
  名称：

  A ribozyme with michaelase activity

  摘要：

  The ability to generate RNA molecules that can catalyze complex organic transformations not only facilitates the reconstruction and plausibility of possible prebiotic reaction pathways but is also crucial for elucidating the potential of the application of RNA catalysts in organic syntheses. Iterative RNA selection previously identified a ribozyme that catalyzes the Michael addition of a cysteine thiol to an alpha,beta-unsaturated amide. This reaction is chemically similar to the rate limiting step of the thymidylate synthase reaction, which is the corresponding reaction of a cysteine thiol to the double-bond of the uracil nucleobase. Here we provide a detailed description of the synthesis of the ribozyme substrates and the substrate oligonucleotides used for its characterization and the investigation of the background reaction. We also describe the further characterization of the ribozyme with respect to substrate specificity. We show that the thiol group of the cysteine nucleophile is essential for the reaction to proceed. When substituted for a thiomethyl group, no reaction takes place. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00311-5