N-n-dodecanoyl-methyl glycinate | 98107-70-1

• 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-n-dodecanoyl-methyl glycinate
• 英文别名: N-lauroyl-glycine methylester；Methyl 2-(dodecanoylamino)acetate
• CAS: 98107-70-1
• 化学式: C₁₅H₂₉NO₃
• mdl: MFCD20928672
• 分子量: 271.4
• InChiKey: VESUBIGIICNRLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.866
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-n-dodecanoyl-methyl glycinate 在 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N-月桂酰甘氨酸
  参考文献：
  名称：

  Structure and Thermotropic Phase Behavior of a Homologous Series ofN-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes

  摘要：

  N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P2(1) space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of oddeven alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between -COOH groups of the molecules from opposite leaflets as well as NH center dot center dot center dot O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 820) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.

  DOI：

  10.1021/cg500481u
• 作为产物：
  描述：

  月桂酸 在 草酰氯 、 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 N-n-dodecanoyl-methyl glycinate
  参考文献：
  名称：

  Structure and Thermotropic Phase Behavior of a Homologous Series ofN-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes

  摘要：

  N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P2(1) space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of oddeven alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between -COOH groups of the molecules from opposite leaflets as well as NH center dot center dot center dot O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 820) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.

  DOI：

  10.1021/cg500481u

文献信息

• METHOD FOR PREPARING LIPOPEPTIDE COMPOUND
  申请人：Kakiuchi Nobuyuki

  公开号：US20120253012A1

  公开（公告）日：2012-10-04

  There is provided a practical method for preparing lipopeptide compounds, which method is capable of inexpensive mass production without requiring complicated operations. The lipopeptide compound of formula (3): is produced by reacting an ester compound of formula (1): with an α-amino acid compound of formula (2): in the presence of a base and within a solvent containing a nonpolar organic solvent.

  提供了一种实用的方法来制备脂肽化合物，该方法能够进行廉价的大规模生产，而不需要复杂的操作。使用式（1）的酯化合物和式（2）的α-氨基酸化合物在含有非极性有机溶剂的溶剂中，在碱的存在下反应，从而产生式（3）的脂肽化合物。
• Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids
  作者：Asish Pal、Yamuna K. Ghosh、Santanu Bhattacharya

  DOI：10.1016/j.tet.2007.05.028

  日期：2007.7

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.
• AMIDES OF MONO AND DICARBOXYLIC ACIDS WITH GLYCOSAMINES, SELECTIVELY ACTIVE ON THE CANNABINOID PERIPHERAL RECEPTOR
  申请人：LIFEGROUP S.p.A.

  公开号：EP0799188B1

  公开（公告）日：1999-09-15
• METHOD FOR THE EXTRACTION AND PURIFICATION OF NUCLEIC ACIDS ON A MEMBRANE
  申请人：Millipore Corporation

  公开号：EP2245157A1

  公开（公告）日：2010-11-03
• US9180201B2
  申请人：——

  公开号：US9180201B2

  公开（公告）日：2015-11-10