Cho-Pro-OH | 3309-52-2

• 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: Cho-Pro-OH
• 英文别名: (2S)-1-cyclohexyloxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 3309-52-2
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: HZCPHBRPOPJWJG-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cho-Pro-OH 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 20.5h， 生成 (S)-cyclohexyl 2-(((6-methylpyridin-2-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  通过空间效应的多维模型预测脂肪酮对映选择性丙炔化反应中的催化剂和底物性能

  摘要：

  新的不对称催化方法的有效性通常取决于以高对映选择性进行反应的不同底物的数量。在这里，我们报告了一项研究，该研究将底物和配体空间效应与脂肪族酮丙炔化的对映选择性相关联。当应用于训练集之外的底物/催化剂组合时，该数学模型显示出高度预测性。

  DOI：

  10.1021/ja4001807
• 作为产物：
  描述：

  L-脯氨酸 、 氯甲酸环己酯 在 sodium hydroxide 作用下， 反应 3.0h， 以62%的产率得到Cho-Pro-OH
  参考文献：
  名称：

  Cyclohexyloxycarbonyl based orthogonal solid phase peptide synthesis in Boc chemistry

  摘要：

  Application of N-cyclohexyloxycarbonyl (Choc) protection in Boc chemistry on solid phase provides a new possibility for the preparation of protected peptide fragments. A Choc/OcHex protection scheme allows also the assembly of cyclic lactam peptides linked to the resin through the C-terminus. Choc protection is stable under the 1M TMSOTf-thioanisole/TFA cleavage condition at 0 degrees C, but it is removable by anhydrous HF. We have utilized cyclohexyloxycarbonyl as an orthogonal protecting group for the synthesis of a i) bicyclic epitope peptide of glycoprotein D of HSV 1 on BHA resin and ii) fully protected hexapeptide involved in protein transport on Merrifield resin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00360-3

文献信息

• Peptide carbocyclic derivatives as inhibitors of the viroporin function of RNA-containing viruses
  作者：V. A. Shibnev、P. G. Deryabin、T. M. Garaev、M. P. Finogenova、A. G. Botikov、D. V. Mishin

  DOI：10.1134/s1068162017050132

  日期：2017.9

  New carbocyclic derivatives of amino acids, peptides, and other compounds have been synthesized, and their antiviral activity toward the influenza A/H5N1 and hepatitis C viruses has been studied in vitro. It has been shown that the aminoacyl derivatives of aminoadamantane are capable of inhibiting the replication of the highly virulent strain of the avian influenza virus (H5N1), which is resistant to aminoadamantanes amantadine and rimantadine. The effect of the configuration of the carbocyclic moiety of the dipeptide H-Pro-Trp-OH on the antiviral properties toward the hepatitis C virus has been studied. The cyclohexyloxycarbonyl derivative of the H-Pro-Trp-OH dipeptide strongly inhibited the replication of HCV in vitro. Some compounds have been found to exhibit a high virucidal activity toward influenza A/H5N1 and HCV virions.