8-mercapto-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)octanamide | 634913-23-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-mercapto-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)octanamide
• 英文别名: 8-mercapto-octanoic acid {2-[2(2-methoxy-ethoxy)-ethoxy]-ethyl}-amide；N-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}-8-sulfanyloctanamide；N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-8-sulfanyloctanamide
• CAS: 634913-23-8
• 化学式: C₁₅H₃₁NO₄S
• 分子量: 321.481
• InChiKey: PXEGTGCTMJGZMO-UHFFFAOYSA-N

物化性质

• 沸点：
  479.8±40.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-mercapto-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)octanamide 在 氧气 作用下， 以 二氯甲烷 为溶剂， 生成 N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-8-[[8-[2-[2-(2-methoxyethoxy)ethoxy]ethylamino]-8-oxooctyl]disulfanyl]octanamide
  参考文献：
  名称：

  Seeing through Macromolecules: T₂-Filtered NMR for the Purity Assay of Functionalized Nanosystems and the Screening of Biofluids

  摘要：

  For samples whose NMR spectra are dominated by the broad signals of macromolecules or functionalized nanoparticles, transverse relaxation (T-2) spectral editing tends itself to a precise identification and determination of small molecules such as metabolites or contaminants. In order to retain the most sensitivity, we propose a method for efficiently removing the interference of spin-spin couplings that typically lead to signal losses in standard pulse schemes designed for T-2. editing.

  DOI：

  10.1021/ja904737r
• 作为产物：
  描述：

  8-溴辛酸 在 盐酸 、 五氟苯酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 50.0h， 生成 8-mercapto-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)octanamide
  参考文献：
  名称：

  Nanoparticle-Based Receptors Mimic Protein-Ligand Recognition

  摘要：

  The self-assembly of a monolayer of ligands on the surface of noble-metal nanoparticles dictates the fundamental nanoparticle's behavior and its functionality. In this combined computational-experimental study, we analyze the structure, organization, and dynamics of functionalized coating thiols in monolayer-protected gold nanoparticles (AuNPs). We explain how functionalized coating thiols self-organize through a delicate and somehow counterintuitive balance of interactions within the monolayer itself and with the solvent. We further describe how the nature and plasticity of these interactions modulate nanoparticle-based chemosensing. Importantly, we found that self-organization of coating thiols can induce the formation of binding pockets in AuNPs. These transient cavities can accommodate small molecules, mimicking protein-ligand recognition, which could explain the selectivity and sensitivity observed for different organic analytes in NMR chemosensing experiments. Thus, our findings advocate for the rational design of tailored coating groups to form specific recognition binding sites on monolayer-protected AuNPs.

  DOI：

  10.1016/j.chempr.2017.05.016

文献信息

• Molecular‐Dynamics‐Simulation‐Directed Rational Design of Nanoreceptors with Targeted Affinity
  作者：Xiaohuan Sun、Laura Riccardi、Federico De Biasi、Federico Rastrelli、Marco De Vivo、Fabrizio Mancin

  DOI：10.1002/anie.201902316

  日期：2019.6.3

  the possibility of rationally designing nanoparticle receptors with targeted affinity and selectivity for specific small molecules. We used atomistic molecular‐dynamics (MD) simulations to gradually mutate and optimize the chemical structure of the molecules forming the coating monolayer of gold nanoparticles (1.7 nm gold‐core size). The MD‐directed design resulted in nanoreceptors with a 10‐fold improvement

  在这里，我们证明了合理设计针对特定小分子具有针对性的亲和力和选择性的纳米粒子受体的可能性。我们使用原子分子动力学（MD）模拟来逐步突变和优化形成金纳米颗粒（1.7纳米金核大小）涂层单层的分子的化学结构。MD导向的设计使纳米受体对目标分析物（水杨酸盐）的亲和力提高了10倍，并且通过从毫摩尔级到微摩尔级的NMR化学传感，检测限降低了100倍。我们可以定义确切的结合模式，该模式具有延长的接触时间和客人深入渗透到单层的功能，以及以暴露的相互作用点为特征的有效结合口袋的独特形状。