N^ε-palmitoyl-lysine methyl ester | 101174-58-7

• 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-palmitoyl-lysine methyl ester
• 英文别名: N(ε)-Palmitoyl-L-lysin-methylester；Nε-palmitoyl-Nα-Cbz-lysine methyl ester hydrochloride；H-L-Lys(Palm)-OMe*HCl；methyl (2S)-2-amino-6-(hexadecanoylamino)hexanoate;hydrochloride
• CAS: 101174-58-7
• 化学式: C₂₃H₄₆N₂O₃*ClH
• 分子量: 435.091
• InChiKey: BNIHHZCYDFFYHP-BOXHHOBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  29
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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-palmitoyl-lysine methyl ester 在 氢溴酸 、 一水合肼 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (L-Lysyl)-
  参考文献：
  名称：

  含有具有抗菌特性的脂肪酸的碱性肽

  摘要：

  概述了新型的表面活性剂的合成，该表面活性剂由在一个氨基上包含一个大的脂族酰基残基的碱性肽组成。组成和抗菌性能之间存在一定的关系。最大限度发挥作用的结构条件是：

  DOI：

  10.1002/hlca.19640470220
• 作为产物：
  描述：

  Nε-palmitoyl-Nα-Cbz-lysine methyl ester 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以82%的产率得到N^ε-palmitoyl-lysine methyl ester
  参考文献：
  名称：

  Cationic surfactants from lysine: Synthesis, micellization and biological evaluation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2008.11.003

文献信息

• Fettsäurehaltige basische Peptide mit antibakterieller Wirkung
  作者：K. Vogler、P. Lanz、P. Quitt、R. O. Studer、W. Lergier、E. Böhni、B. Fust

  DOI：10.1002/hlca.19640470220

  日期：——

  The synthesis of a new class of surface active agents consisting of basic peptides containing on one amino group a large aliphatic acyl residue is outlined. There are some definite relations between constitution and antibacterial properties. The structural conditions for maximum activity are:

  概述了新型的表面活性剂的合成，该表面活性剂由在一个氨基上包含一个大的脂族酰基残基的碱性肽组成。组成和抗菌性能之间存在一定的关系。最大限度发挥作用的结构条件是：
• 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.