melittin | 123168-46-7

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: melittin
• 英文别名: GIGAVLKVLTTGLPALISWIKRKRQQ
• CAS: 123168-46-7
• 化学式: C₁₃₁H₂₂₈N₃₈O₃₂
• 分子量: 2847.49
• InChiKey: SPOIKCKBWYREHS-JFTDCZMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  201
• 可旋转键数：
  99
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  1150
• 氢给体数：
  41
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  melittin 、 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