Nα-lauroylnitroarginine-Nα-lysine(Cbz) methyl ester | 143486-77-5

• 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: Nα-lauroylnitroarginine-Nα-lysine(Cbz) methyl ester
• 英文别名: lauroyl-Arg(NO2)-Lys(Cbz)-OMe；methyl (2S)-2-[[(2S)-2-(dodecanoylamino)-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 143486-77-5
• 化学式: C₃₃H₅₅N₇O₈
• 分子量: 677.842
• InChiKey: RYPKLCICARIQKR-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  48
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  219
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Nα-lauroylnitroarginine-Nα-lysine(Cbz) methyl ester 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以91%的产率得到Nα-lauroylarginine-Nα-lysine methyl ester dihydrochloride
  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：

  (S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate 、 Nα-lauroylnitroarginine amine 在 三乙烯二胺 、 (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到Nα-lauroylnitroarginine-Nα-lysine(Cbz) 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 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.