N-(10-undecenoyl)-L-valine

• 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: N-(10-undecenoyl)-L-valine
• 英文别名: N-undec-10'-enoyl-L-valine；undecylenyl-L-valine；(2S)-3-methyl-2-(undec-10-enoylamino)butanoic acid
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: CUMDGPLYIACIIS-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(10-undecenoyl)-L-valine 、 (S)-(-)- α-甲基苄胺 生成 N-[(2S)-3-methyl-1-oxo-1-[[(1S)-1-phenylethyl]amino]butan-2-yl]undec-10-enamide
  参考文献：
  名称：

  ZHAN, ZHENG-YUN;ZHOU, LIANG-MO, XUASYUEH SYUEHBAO, 48,(1990) N1, S. 1127-1130

  摘要：

  DOI：
• 作为产物：
  描述：

  L-缬氨酸 、 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64%的产率得到N-(10-undecenoyl)-L-valine
  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

• Enantiomeric Separation with Sodium Dodecanoyl-L-amino Acidate Micelles and Poly(sodium (10-undecenoyl)-L-valinate) by Electrokinetic Chromatography
  作者：Akira. Dobashi、Masaki. Hamada、Yasuo. Dobashi、Junko. Yamaguchi

  DOI：10.1021/ac00113a040

  日期：1995.9.1

  The sodium salts of N-dodecanoylated L-valine, L-alanine, and L-threonine formed micelles which were then used to resolve enantiomeric 3,5-dinitrobenzoylated amino acid isopropyl esters and amines by electrokinetic chromatography (EKC). Hydrophobicity of the micellar core essential for enantiomer separation was observed with the concentration dependence of NMR chemical shift of amide protons in the surfactants, The amide functionality in chiral micelles was found to be shielded from bulk water. This functionality is thus capable of serving as a hydrogen bonding site, The elution order of separated amino acid derivatives, the D enantiomer eluting faster than the corresponding L enantiomer, indicates that the chiral micelle binds to the L enantiomer, having the same configuration as its chiral component to a greater extent than the D counterpart. In the following, this is discussed in terms of differences in the perturbation of the micellar structure produced by enantiomer penetration. The photopolymerization of vinyl group-terminated chiral surfactants, analogous to the above surfactant derived fi om L-valine, gave rise to micelle-like polymers with constraints imposed by the covalently linked tails of surfactant monomers. This poly(sodium(10-undecenoyl)-L-valinate) showed chromatographic resolution behavior similar to that of chiral micelles in EKC, indicating that chiral recognition is possible through the explicit polymolecular structure independent of the dynamic association-dissociation equilibrium of ordinal surfactants in the bulk water phase.
• 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.
• ZHAN, ZHENG-YUN;ZHOU, LIANG-MO, XUASYUEH SYUEHBAO, 48,(1990) N1, S. 1127-1130
  作者：ZHAN, ZHENG-YUN、ZHOU, LIANG-MO

  DOI：——

  日期：——
• ——
  作者：FABIAN G.、 SCHIERHORN M.、 PORSCHMANN J.、 KRAUS G.、 ALTMANN H.、 ZASCHKE H.

  DOI：——

  日期：——
• JPH04149205A
  申请人：——

  公开号：JPH04149205A

  公开（公告）日：1992-05-22