3-hydroxy-2-stearamidopropanoic acid

• 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: 3-hydroxy-2-stearamidopropanoic acid
• 英文别名: octadecanoyl-L-serine；N-stearoyl L-serine；N-stearoyl-L-serine；N-stearoylserine；N-stearoyl serine；(2S)-3-hydroxy-2-(octadecanoylamino)propanoic acid
• 化学式: C₂₁H₄₁NO₄
• 分子量: 371.561
• InChiKey: CLHUCXCVFSEJRR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (S)-N-octadecanoyl-serinate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 3-hydroxy-2-stearamidopropanoic acid
  参考文献：
  名称：

  新的N-酰基氨基酸和可再生脂肪酸的衍生物：烃的凝胶化和热学性质

  摘要：

  这项工作报告了从C16：0，C18：0，C18：1和C18：1（OH）脂肪酸家族合成新的脂肪N-酰基氨基酸和N-酰基氨基酯的过程，并证明了这些化合物作为有机凝胶的活性代理商。将化合物加热溶解在各种溶剂中（Ñ己烷，甲苯和汽油）。只有饱和C16：0和C18：从丙氨酸衍生0能够形成凝胶的甲苯溶液，和饱和的C16：从苯丙氨酸衍生的0表明胶凝Ñ正己烷。这是l的脂肪N-酰基氨基酯和N-酰基氨基酸衍生物的第一个证据-丝氨酸和脂肪酸C16：0，C18：0和C18：1能够与己烷形成凝胶。该观察证实了1-丝氨酸的片段衍生物中的羟基在形成良好凝胶中的重要性。

  DOI：

  10.1016/j.tetlet.2012.03.015

文献信息

• Synthesis of Lipoamino Acids and Their Activity against Cerebral Ischemic Injury
  作者：Li-Yun Yao、Qi Lin、Yin-Yao Niu、Ke-Min Deng、Jian-Hua Zhang、Yang Lu

  DOI：10.3390/molecules14104051

  日期：——

  A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1–10 M.

  一系列脂氨基酸被合成，并评估了它们对大鼠脑片由氧葡萄糖剥夺（OGD）诱导的脑缺血的神经保护作用。在这些化合物中，N-硬脂酰基-L-酪氨酸（4）、N-硬脂酰基-L-丝氨酸（5）和N-硬脂酰基-L-苏氨酸（6）表现出了良好的神经保护活性。我们发现，脂氨基酸的神经保护活性依赖于酰基团、氨基酸支链上自由羧基和自由羟基的存在。结果还显示，5是最活跃的化合物，在1-10 M的范围内保护大鼠脑片免受OGD和过氧化氢（H2O2）的损伤。
• The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid L-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells
  作者：Li Yun Grace Lim、Yingying Su、Filip Braet、Pall Thordarson

  DOI：10.1071/ch09211

  日期：——

  A series of saturated and unsaturated fatty acid l-serines 3 were synthesized and their ability to form self-assembled gels was investigated. The saturated (lauroyl 3a and steraoyl 3b) and monounsaturated (oleoyl 3c) fatty acid l-serines form gels in both water and organic solvent, whereas the diunsaturated linoleyl-l-serine 3d does not form gels in these solvents, indicating that unsaturation adversely affects the gelation process. Cytotoxicity studies on these compounds with Caco-2 cancer cells in vitro show that these gels are only moderately cytotoxic at concentrations up to 0.5 mM, making them a promising candidate for applications such as drug delivery.

  研究人员合成了一系列饱和和不饱和脂肪酸 l-丝氨酸 3，并考察了它们形成自组装凝胶的能力。饱和（月桂酰基 3a 和链烷基 3b）和单不饱和（油酰基 3c）脂肪酸 l-丝氨酸在水和有机溶剂中都能形成凝胶，而二不饱和亚油酰基 l-丝氨酸 3d 在这些溶剂中不能形成凝胶，这表明不饱和会对凝胶过程产生不利影响。用 Caco-2 癌细胞对这些化合物进行的体外细胞毒性研究表明，当浓度达到 0.5 毫摩尔时，这些凝胶仅具有适度的细胞毒性，使它们成为药物递送等应用的理想候选物质。
• Enantioselective crystallization in miniemulsions based on chiral surfactants
  作者：Tali Menahem、Yitzhak Mastai

  DOI：10.1039/b800211h

  日期：——

  resolution of racemic compounds by crystallization. Chiral surfactants based on N-stearoyl acid were synthesized and used in order to form a chiral micellar system of calcium tartrate tetrahydrate (CaT) crystallization. It is shown for a chiral model system of CaT that crystallization in chiral miniemulsions leads to kinetic chiral resolution. In addition, crystallization in chiral miniemulsion results

  在这封信中，我们描述了一种手性胶束系统在消旋外消旋化合物的光学拆分中的新应用。 结晶。手性表面活性剂基于N-硬脂酸的合成并用于形成手性胶束系统。四水酒石酸钙 （猫） 结晶。对于CaT的手性模型系统显示，结晶手性细乳剂中的化合物导致动力学手性拆分。此外，结晶 手性细乳液中的α-氨基丁酸酯导致晶体形态改变。
• Shinitzky, Meir; Haimovitz, Rachel, Journal of the American Chemical Society, 1993, vol. 115, # 26, p. 12545 - 12549
  作者：Shinitzky, Meir、Haimovitz, Rachel

  DOI：——

  日期：——
• Potential Neuroprotective Drugs in Cerebral Ischemia: New Saturated and Polyunsaturated Lipids Coupled to Hydrophilic Moieties: Synthesis and Biological Activity
  作者：Alain César Biraboneye、Sébastien Madonna、Younes Laras、Slavica Krantic、Pamela Maher、Jean-Louis Kraus

  DOI：10.1021/jm900227u

  日期：2009.7.23

  The ganglioside GM1 has neuroprotective effects but is not of therapeutic value because of its lack of bioavailability. Thus, molecules that mimic GM I represent a novel approach to neuroprotection. We have synthesized 19 small GM1-like analogues whose simplified structure includes a hydrophobic saturated or unsaturated moiety linked to a hydrophilic moiety. We report their neuroprotective effects in two distinct models of nerve cell death using hippocampus-derived HT22 cells. We found that several analogues protected the HT22 cells from death at concentrations ranging from 2 to 5 mu M. Additional neuroprotective assays using cortical slices injured by glutamate confirmed these results. Since members of the MAP kinase family are known to be key players in nerve cell survival and death, we characterized the role of these kinases in the neuroprotective mechanisms of the GM1-like analogues. Interestingly, the results indicate that the compounds provide neuroprotection through distinct mechanisms of action.