纤连蛋白粘附促进肽 | 125720-21-0

• 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
• 中文名称: 纤连蛋白粘附促进肽
• 英文名称: WQPPRARI
• 英文别名: H-Trp-Gln-Pro-Pro-Arg-Ala-Arg-Ile-OH；trp-Gln-Pro-Pro-Arg-Ala-Arg-Ile；heparin-binding peptide；Fibronectin Adhesion-promoting Peptide；(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylpentanoic acid
• CAS: 125720-21-0
• 化学式: C₄₇H₇₄N₁₆O₁₀
• 分子量: 1023.21
• InChiKey: OVXIMRGEBNSORH-PJRZOMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  73
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  437
• 氢给体数：
  13
• 氢受体数：
  13

制备方法与用途

生物活性

Fibronectin Adhesion-promoting Peptide（肝素结合肽）是一种存在于纤连蛋白C端肝素结合域中的氨基酸序列。这种肽能够促进间充质干细胞(MSC)球状体组装成更大的聚集体，并通过与细胞的肝素结合区反应直接促进内皮细胞的粘附、扩散和迁移。

体外研究

GRGDS 和 Fibronectin Adhesion-promoting Peptide（肝素结合肽：WQPPRARI）微图案能够增加假体材料的内皮化。Fibronectin Adhesion-promoting Peptide 还增强了趋化性细胞迁移。纤连蛋白的抗凋亡作用需要 WQPPRARI 序列的存在，这可能是由于该序列和 RGD 动力学共同介导的协同生存信号。RDGS 和 Fibronectin Adhesion-promoting Peptide 通过不同的激活途径促进细胞黏附，诱导不同形式的黏着，可以通过分析焦点接触和纤维状接触来突出显示这些差异。

反应信息

• 作为反应物：
  描述：

  纤连蛋白粘附促进肽 、 邻氨基对甲苯酚 在 potassium hexacyanoferrate(III) 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  N-Terminal Modification of Proteins with o-Aminophenols

  摘要：

  The synthetic modification of proteins plays an important role in chemical biology and biomaterials science. These fields provide a constant need for chemical tools that can introduce new functionality in specific locations on protein surfaces. In this work, an oxidative strategy is demonstrated for the efficient modification of N-terminal residues on peptides and N-terminal proline residues on proteins. The strategy uses o-aminophenols or o-catechols that are oxidized to active coupling species in situ using potassium ferricyanide. Peptide screening results have revealed that many N-terminal amino acids can participate in this reaction, and that proline residues are particularly reactive. When applied to protein substrates, the reaction shows a stronger requirement for the proline group. Key advantages of the reaction include its fast second-order kinetics and ability to achieve site-selective modification in a single step using low concentrations of reagent. Although free cysteines are also modified by the coupling reaction, they can be protected through disulfide formation and then liberated after N-terminal coupling is complete. This allows access to doubly functionalized bioconjugates that can be difficult to access using other methods.

  DOI：

  10.1021/ja500728c

文献信息

• Latent reactive polymers with biologically active moieties
  申请人：SurModics, Inc.

  公开号：EP1577670A2

  公开（公告）日：2005-09-21

  The present invention relates to a polybifunctional reagent having a polymeric backbone, one or more pendent photoreactive moieties, and two or more pendent bioactive groups. The reagent can be activated to form a bulk material or can be brought into contact with the surface of a previously formed biomaterial and activated to form a coating. The pendent bioactive groups function by promoting the attachment of specific molecules or cells to the bulk material or coated surface. Bioactive groups can include proteins, peptides, carbohydrates, nucleic acids and other molecules that are capable of binding noncovalently to specific and complimentary portions of molecules or cells.

  本发明涉及一种具有聚合物骨架、一个或多个下垂光活性分子和两个或多个下垂生物活性基团的多官能团试剂。该试剂可以活化形成块状材料，也可以与先前形成的生物材料表面接触并活化形成涂层。悬垂生物活性基团通过促进特定分子或细胞附着到主体材料或涂层表面来发挥作用。生物活性基团可包括蛋白质、肽、碳水化合物、核酸和其他能够与分子或细胞的特定和互补部分非共价结合的分子。
• POLYPEPTIDES WITH FIBRONECTIN ACTIVITY
  申请人：THE REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：EP0366728A1

  公开（公告）日：1990-05-09
• POLYPEPTIDES USEFUL FOR TREATING INFLAMMATORY DISORDERS
  申请人：THE REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：EP0673384A1

  公开（公告）日：1995-09-27
• EP0673384A4
  申请人：——

  公开号：EP0673384A4

  公开（公告）日：1996-10-09
• LATENT REACTIVE POLYMERS WITH BIOLOGICALLY ACTIVE MOIETIES
  申请人：SurModics, Inc.

  公开号：EP1003561A2

  公开（公告）日：2000-05-31