2-acryloylamido-6-phenylacetamidopyridine | 1096712-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-acryloylamido-6-phenylacetamidopyridine
• 英文别名: N-[6-[(2-phenylacetyl)amino]pyridin-2-yl]prop-2-enamide
• CAS: 1096712-45-6
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: GAFIVSWYEMNDFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-acryloylamido-6-phenylacetamidopyridine
  参考文献：
  名称：

  Affinity adsorption mechanism studies of adsorbents C1-Zn(II) for uremic middle molecular peptides containing Asp-Phe-Leu-Ala-Glu sequence

  摘要：

  为了利用高效的吸附剂去除含有DFLAE（DE5，一种典型的在尿毒症血清中积累的肽序列）序列的中分子肽，我们设计并合成了三种亲和力吸附剂（C1-Zn2+、C2-Zn2+ 和 C3-Zn2+），它们对DE5具有很高的亲和力。随后，我们通过静态吸附实验和等温滴定量热法（ITC）评估了每种吸附剂的相应吸附能力。结果显示，C1-Zn2+对含DE5的肽具有最佳的吸附能力，DE5的吸附能力为8.52 mg/g。通过改变吸附条件，阐明了吸附机制。吸附的主要驱动力是金属-羧酸协调作用，而疏水作用提供了协同效应。预计我们目前的研究工作能够为设计具有高亲和力和选择性的低聚肽吸附剂提供基础理解。

  DOI：

  10.1007/s11426-010-4193-7

文献信息

• Adsorbents with High Selectivity for Uremic Middle Molecular Peptides Containing the Asp-Phe-Leu-Ala-Glu Sequence
  作者：Yitao Qiao、Jianxin Zhao、Pinglin Li、Jun Wang、Jing Feng、Wei Wang、Hongwei Sun、Yi Ma、Zhi Yuan

  DOI：10.1021/la904272e

  日期：2010.5.18

  Asp-Phe-Leu-Ala-Glu (DES) is a frequent sequence of many toxic middle molecular peptides that accumulate in uremic patients. To eliminate these peptides by hemoperfusion, three adsorbents (CP1-Zn(2+), CP2-Zn(2+), and CP3-Zn(2+)) were designed on the basis of coordination and hydrophobic interactions. Adsorption experiments indicated that CP2-Zn(2+) had the highest affinity for DES among these three adsorbents. Also, the adsorption capacity of CP2-Zn(2+) in DES and DES-containing peptides was about 2-6 times higher than that of peptides without the DES sequence. Linear polymers bearing the same functional groups of the adsorbents were used as models to study the adsorption mechanism via isothermal titration calorimetry (ITC) and computer-aided analyses. The results indicated that coordination and hydrophobic interactions played the most important roles in their affinity. When two carboxyl moieties on Asp and Glu residues coordinated to CP2-Zn(2+), the hydrophobic interaction took place by the aggregation of the hydrophobic amino acid residues with phenyl group on CP2-Zn(2+). The optimal collaboration of these interactions led to the tight binding and selective adsorption of DE5-containing peptides onto CP2-Zn(2+). These results may provide new insight into the design of affinity adsorbents for peptides containing DES-like sequences.
• Affinity adsorption mechanism studies of adsorbents C1-Zn(II) for uremic middle molecular peptides containing Asp-Phe-Leu-Ala-Glu sequence
  作者：PingLin Li、LiXue Fu、YiTao Qiao、JianXin Zhao、Wei Wang、Zhi Yuan

  DOI：10.1007/s11426-010-4193-7

  日期：2011.2

  To exploit efficient adsorbents for removing middle molecular peptides containing DFLAE (DE5, a typical peptide sequence accumulated in uremic serum) sequence by hemoperfusion, we designed and synthesized three affinity adsorbents (C1-Zn2+, C2-Zn2+ and C3-Zn2+) that could have high affinity to DE5. Subsequently, we evaluated the corresponding adsorption ability of each adsorbent by static adsorption experiments and isothermal titration calorimetry (ITC). The results showed that C1-Zn2+ had the best adsorption ability to DE5-containing peptides and the adsorption capacity for DE5 was 8.52 mg/g. By changing the adsorption conditions, the adsorption mechanism was elucidated. The main driving force of the adsorption is metal-carboxyl coordination and the hydrophobic force affords the cooperative effect. It is expected that our present work can provide basic understanding for the design of adsorbents with high affinity and selectivity towards oligopeptides.

  为了利用高效的吸附剂去除含有DFLAE（DE5，一种典型的在尿毒症血清中积累的肽序列）序列的中分子肽，我们设计并合成了三种亲和力吸附剂（C1-Zn2+、C2-Zn2+ 和 C3-Zn2+），它们对DE5具有很高的亲和力。随后，我们通过静态吸附实验和等温滴定量热法（ITC）评估了每种吸附剂的相应吸附能力。结果显示，C1-Zn2+对含DE5的肽具有最佳的吸附能力，DE5的吸附能力为8.52 mg/g。通过改变吸附条件，阐明了吸附机制。吸附的主要驱动力是金属-羧酸协调作用，而疏水作用提供了协同效应。预计我们目前的研究工作能够为设计具有高亲和力和选择性的低聚肽吸附剂提供基础理解。