[2-(ethyldisulfanyl)phenyl] (2S)-pyrrolidine-2-carboxylate | 1262584-78-0

• 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: [2-(ethyldisulfanyl)phenyl] (2S)-pyrrolidine-2-carboxylate
• CAS: 1262584-78-0
• 化学式: C₁₃H₁₇NO₂S₂
• 分子量: 283.415
• InChiKey: WEUMNVMZJQXGEE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(ethyldisulfanyl)phenyl] (2S)-pyrrolidine-2-carboxylate 、 (2S)-5-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-4-carboxy-2-[[(2S)-3-(1H-indol-3-yl)-2-[[(2S,4R)-4-sulfanylpyrrolidine-2-carbonyl]amino]propanoyl]amino]butanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid 反应 3.0h， 以73%的产率得到(2S)-5-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-4-carboxy-2-[[(2S)-3-(1H-indol-3-yl)-2-[[(2S,4R)-1-[(2S)-pyrrolidine-2-carbonyl]-4-sulfanylpyrrolidine-2-carbonyl]amino]propanoyl]amino]butanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  An Advance in Proline Ligation

  摘要：

  Native chemical ligation (NCL) is widely applicable for building proteins in the laboratory. Since the discovery of this method, many strategies have been developed to enhance its capability and efficiency. Because of the poor reactivity of proline thioesters, ligation at a C-terminal proline site is not readily accomplished. Here, we demonstrate that ligation at an N-terminal protein is feasible using the combined logic of NCL and metal-free dethiylation (MFD).

  DOI：

  10.1021/ja204277b

文献信息

• Advances in Proline Ligation
  作者：Steven D. Townsend、Zhongping Tan、Suwei Dong、Shiying Shang、John A. Brailsford、Samuel J. Danishefsky

  DOI：10.1021/ja212182q

  日期：2012.2.29

  Application of native chemical ligation logic to the case of an N-terminal proline is described. Two approaches were studied. One involved incorporation of a 3R-substituted thiyl-proline derivative. Improved results were obtained from a 3R-substituted selenol function, incorporated in the context of an oxidized dimer.