N^ε-myristoyl-lysine methyl ester | 1015842-45-1

• 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^ε-myristoyl-lysine methyl ester
• 英文别名: Nε-myristoyl-Nα-Cbz-lysine methyl ester hydrochloride；methyl (2S)-2-amino-6-(tetradecanoylamino)hexanoate;hydrochloride
• CAS: 1015842-45-1
• 化学式: C₂₁H₄₂N₂O₃*ClH
• 分子量: 407.037
• InChiKey: DMVMXAZZSWWSJJ-FYZYNONXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  81.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N^ε-myristoyl-lysine methyl ester 、 硫酸二甲酯 在 potassium carbonate 、 盐酸 作用下， 以 甲醇 为溶剂， 以70%的产率得到[(2S)-1-methoxy-1-oxo-6-(tetradecanoylamino)hexan-2-yl]-trimethylazanium;chloride
  参考文献：
  名称：

  Cationic Surfactants Derived from Lysine: Effects of Their Structure and Charge Type on Antimicrobial and Hemolytic Activities

  摘要：

  Three different sets of cationic surfactants from lysine have been synthesized. The first group consists of three monocatenary surfactants with one lysine as the cationic polar head with one cationic charge. The second consists of three monocatenary surfactants with two amino acids as cationic polar head with two positive charges. Finally, four gemini surfactants were synthesized in which the spacer chain and the number and type of cationic charges have been regulated. The micellization process, antimicrobial activity, and hemolytic activity were evaluated. The critical micelle concentration was dependent only on the hydrophobic character of the molecules. Nevertheless, the antimicrobial and hemolytic activities were related to the structure of the compounds as well as the type of cationic charges. The most active surfactants against the bacteria were those with a cationic charge on the trimethylated amino group, whereas all of these surfactants showed low hemolytic character.

  DOI：

  10.1021/jm101315k
• 作为产物：
  描述：

  Nε-myristoyl-Nα-Cbz-lysine methyl ester 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N^ε-myristoyl-lysine methyl ester
  参考文献：
  名称：

  Cationic Surfactants Derived from Lysine: Effects of Their Structure and Charge Type on Antimicrobial and Hemolytic Activities

  摘要：

  Three different sets of cationic surfactants from lysine have been synthesized. The first group consists of three monocatenary surfactants with one lysine as the cationic polar head with one cationic charge. The second consists of three monocatenary surfactants with two amino acids as cationic polar head with two positive charges. Finally, four gemini surfactants were synthesized in which the spacer chain and the number and type of cationic charges have been regulated. The micellization process, antimicrobial activity, and hemolytic activity were evaluated. The critical micelle concentration was dependent only on the hydrophobic character of the molecules. Nevertheless, the antimicrobial and hemolytic activities were related to the structure of the compounds as well as the type of cationic charges. The most active surfactants against the bacteria were those with a cationic charge on the trimethylated amino group, whereas all of these surfactants showed low hemolytic character.

  DOI：

  10.1021/jm101315k

文献信息

• Cationic surfactants from lysine: Synthesis, micellization and biological evaluation
  作者：Lourdes Pérez、Aurora Pinazo、M. Teresa García、Marina Lozano、Angeles Manresa、Marta Angelet、M. Pilar Vinardell、Montse Mitjans、Ramon Pons、M. Rosa Infante

  DOI：10.1016/j.ejmech.2008.11.003

  日期：2009.5

  Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of N-epsilon-lauroyl lysine methyl ester, N-epsilon-myristoyl lysine methyl ester and N-epsilon-palmitoyl lysine methyl ester) have been prepared in high yields by lysine acylation in F position with three natural saturated fatty acids. The micellization process of these surfactants has been studied using the PGSE-NMR technique. The compounds were tested as antimicrobial agents against Gram-positive and Gram-negative bacteria. The surfactants show moderate antimicrobial activity against the Gram-positive bacteria but Gram-negative bacteria are resistant to these surfactants in the concentration range tested. The haemolytic activity is considerably lower than those reported for other cationic N-alpha-acyl amino acid analogues. The acute toxicity against Daphnia magna and biodegradability was studied. The toxicity is clearly lower than that reported for conventional cationic surfactants from quaternary ammonium and the three surfactants from lysine can be classified as ready biodegradable surfactants. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Cationic Surfactants Derived from Lysine: Effects of Their Structure and Charge Type on Antimicrobial and Hemolytic Activities
  作者：A. Colomer、A. Pinazo、M. A. Manresa、M. P. Vinardell、M. Mitjans、M. R. Infante、L. Pérez

  DOI：10.1021/jm101315k

  日期：2011.2.24

  Three different sets of cationic surfactants from lysine have been synthesized. The first group consists of three monocatenary surfactants with one lysine as the cationic polar head with one cationic charge. The second consists of three monocatenary surfactants with two amino acids as cationic polar head with two positive charges. Finally, four gemini surfactants were synthesized in which the spacer chain and the number and type of cationic charges have been regulated. The micellization process, antimicrobial activity, and hemolytic activity were evaluated. The critical micelle concentration was dependent only on the hydrophobic character of the molecules. Nevertheless, the antimicrobial and hemolytic activities were related to the structure of the compounds as well as the type of cationic charges. The most active surfactants against the bacteria were those with a cationic charge on the trimethylated amino group, whereas all of these surfactants showed low hemolytic character.