undecylenyl-L-alanine

• 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: undecylenyl-L-alanine
• 英文别名: (2S)-2-(undec-10-enoylamino)propanoic acid
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.357
• InChiKey: SWGXIJOBHFOVOL-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-丙氨酸 、 N-hydroxysuccinimide ester of undecylinic acid 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以79%的产率得到undecylenyl-L-alanine
  参考文献：
  名称：

  Synthesis of polymerized N-Undecylenyl-L-aminoacid and N-Undecylenyl-L-peptide derivatives

  摘要：

  Micelle forming polymerized N-Undecylenyl-L-aminoacid and N-Undecylenyl-L-peptide derivatives have been obtained. These compounds are effective as pseudostationary phases in electrokinetic capillary electrophoresis for racemate resolution. Synthetic procedures are described in detail, as well as preliminary analytical data comparing aminoacid derivatives and an aminoacid derivative with a peptide derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02471-x

文献信息

• Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. Part 2. Polymerized Anionic Surfactants Derived from Amino Acids and Dipeptides
  作者：A. Leydet、H. El Hachemi、B. Boyer、G. Lamaty、J. P. Roque、D. Schols、R. Snoeck、G. Andrei、S. Ikeda、J. Neyts、D. Reymen、J. Este、M. Witvrouw、E. De Clercq

  DOI：10.1021/jm950358j

  日期：1996.1.1

  A series of new polyanions was synthesized via gamma-polymerization, in aqueous micellar solution, of omega-unsaturated anionic surfactants whose polar head was derived from amino acids or dipeptides. The obtained polyanions were evaluated for their activity against human immunodeficiency virus (HIV-1, HIV-2) and various other RNA and DNA viruses. All the test compounds proved active against HIV-1 and HIV-2, their 50% inhibitory concentration (IC50) being in the range of 0.04-7.5 mu g/mL, while they were not toxic to the host cells (CEM-4 or MT-4) at concentrations up to 100 mu g/mL or higher. The HIV-inhibitory effect increased with the hydrophilic character of the amino acid moiety. The compounds were found to interact with both the viral envelope glycoprotein gp120 and the cellular CD4 receptor, thus blocking virus-cell binding and virus-induced syncytium formation. These polyanions also proved active against human cytomegalovirus at about the same IC50 as for HIV. In addition, they were also active, albeit at somewhat higher IC50 values (0.8-20 mu g/mL), against other enveloped viruses such as respiratory syncytial virus and arenaviruses (Junin and Tacaribe). At yet higher IC50 values (greater than or equal to 20 mu g/mL), some of the compounds showed activity against influenza A virus. No activity was observed with any of the compounds against vesicular stomatitis virus, Sindbis virus, Semliki forest virus, influenza B, parainfluenza type 3, and the nonenveloped viruses Coxsackie type B4, polio type 1, and reovirus type 1.
• Synthesis of polymerized N-Undecylenyl-L-aminoacid and N-Undecylenyl-L-peptide derivatives
  作者：Javier Macossay、Shahab A. Shamsi、Isiah M. Warner

  DOI：10.1016/s0040-4039(98)02471-x

  日期：1999.1

  Micelle forming polymerized N-Undecylenyl-L-aminoacid and N-Undecylenyl-L-peptide derivatives have been obtained. These compounds are effective as pseudostationary phases in electrokinetic capillary electrophoresis for racemate resolution. Synthetic procedures are described in detail, as well as preliminary analytical data comparing aminoacid derivatives and an aminoacid derivative with a peptide derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.