pentadecanoylglycine | 155300-71-3

• 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: pentadecanoylglycine
• 英文别名: 2-(pentadecanoylamino)acetic acid
• CAS: 155300-71-3
• 化学式: C₁₇H₃₃NO₃
• 分子量: 299.454
• InChiKey: GFPGAMQTXLSWHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  十五烷酸 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 pentadecanoylglycine
  参考文献：
  名称：

  Novel Peak Shift Correction Method Based on the Retention Index for Peak Alignment in Untargeted Metabolomics

  摘要：

  DOI：

  10.1021/acs.analchem.3c02583

文献信息

• Process for converting primary amidoalcohols to amidocarboxylic acids in high yield
  申请人：Conopco, Inc.

  公开号：US07307187B1

  公开（公告）日：2007-12-11

  The invention relates to an improved process for oxidizing a primary amidoalcohol to the corresponding amidocarboxylic acid in high yield.

  本发明涉及一种改进的方法，用于将一种原始的氨基醇氧化为相应的酰胺羧酸，高收率。
• Enzyme Engineering for High‐Yielding Amide Formation: Lipase‐Catalyzed Synthesis of <i>N</i> ‐Acyl Glycines in Aqueous Media
  作者：Glen Kai Bin Kua、Giang Kien Truc Nguyen、Zhi Li

  DOI：10.1002/anie.202217878

  日期：2023.3.27

  N-acyl glycines are essential biosurfactants in cosmetics and pharmaceuticals. Their commercial production involves the use of neurotoxic phosgene. Aiming towards green synthesis of these amides, we developed a novel amide synthesis concept involving glycerol activation and evolved a hydrolytic enzyme by reshaping its catalytic pocket into a highly active amide bond-forming enzyme, displaying 400-fold

  N-酰基甘氨酸是化妆品和药物中必不可少的生物表面活性剂。它们的商业生产涉及使用具有神经毒性的光气。为了实现这些酰胺的绿色合成，我们开发了一种涉及甘油活化的新型酰胺合成概念，并通过将其催化袋重塑为高活性酰胺键形成酶，进化出一种水解酶，显示出 400 倍的 N-月桂酰甘氨酸合成催化效率收率超过 80%。
• 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