N-arachidoyl glycine | 617703-96-5

• 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: N-arachidoyl glycine
• 英文别名: arachidoyl glycine；N-eicosanoylglycine；Arachidoyl glycine；2-(icosanoylamino)acetic acid
• CAS: 617703-96-5
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: MUNNIYAZGQGMQR-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMF：20 mg/ml； DMSO：15 mg/ml；乙醇：25 mg/ml； PBS（pH 7.2）：2 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  26
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二十酸 在 草酰氯 、 碳酸氢钠 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 4.0h， 生成 N-arachidoyl glycine
  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

• [EN] INSULIN DERIVATIVE<br/>[FR] DÉRIVÉ D'INSULINE<br/>[ZH] 胰岛素衍生物
  申请人：GAN & LEE PHARMACEUTICALS

  公开号：WO2021136293A1

  公开（公告）日：2021-07-08

  一种胰岛素衍生物，其药物制剂、其与长效GLP-1化合物的药物组合物、及所述酰化胰岛素、药物制剂和药物组合物的医药用途。所述胰岛素衍生物相比于德谷胰岛素或其它胰岛素衍生物，具有预料不到的显著增加的药效、具有更长的持续作用时间、更长的体内半衰期、良好的生物利用率、及具有更好的物理稳定性、化学稳定性。
• [EN] LONG-ACTING GLP-1 COMPOUND<br/>[FR] COMPOSÉ GLP-1 À ACTION PROLONGÉE<br/>[ZH] 长效GLP-1化合物
  申请人：GAN & LEE PHARMACEUTICALS

  公开号：WO2021136303A1

  公开（公告）日：2021-07-08

  一种新的GLP-1衍生物，其相比于利拉鲁肽、索玛鲁肽等已上市的GLP-1衍生物，具有相当或更好的效力、药效或功效、更长或相当的体内持续作用时间或体内半衰期、具有更好或相当的GLP-1受体结合亲和力、具有更好或相当的DPP-IV稳定性。
• Structure and Thermotropic Phase Behavior of a Homologous Series of<i>N</i>-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes
  作者：S. Thirupathi Reddy、Krishna Prasad Krovi、Musti J. Swamy

  DOI：10.1021/cg500481u

  日期：2014.10.1

  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.
• Novel Peak Shift Correction Method Based on the Retention Index for Peak Alignment in Untargeted Metabolomics
  作者：Jun-Di Hao、Yao-Yu Chen、Yan-Zhen Wang、Na An、Pei-Rong Bai、Quan-Fei Zhu、Yu-Qi Feng

  DOI：10.1021/acs.analchem.3c02583

  日期：2023.9.5