1(N)-formyl-trpH | 74257-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1(N)-formyl-trpH
• 英文别名: (+/-)-N^ι-Formyltryptophan；Nⁱ-formyl-tryptophan；N^In-Formyl-tryptophan；2-azaniumyl-3-(1-formylindol-3-yl)propanoate
• CAS: 74257-18-4
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: KRUDZOGZZBVSHD-UHFFFAOYSA-N

物化性质

• 沸点：
  477.9±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1(N)-formyl-trpH 生成 (+/-)-N^ι-Formyl-N^α-BOC-tryptophan tert-butyl ester
  参考文献：
  名称：

  Selective Removal of an N-BOC Protecting Group in the Presence of a tert-Butyl Ester and Other Acid-Sensitive Groups

  摘要：

  DOI：

  10.1021/jo00090a045
• 作为产物：
  描述：

  Boc-Trp(For) 在 对甲酚 、 二甲基硫 、 氢氟酸 作用下， 反应 1.0h， 以2%的产率得到DL-色氨酸
  参考文献：
  名称：

  改进固相肽合成中的脱保护作用：在Me 2 S–对-硫代甲酚混合物中低浓度的HF中将N i-甲酰基-色氨酸脱保护为色氨酸

  摘要：

  所述Ñ我-formy保护在固相肽合成色氨酸组被发现可以通过一个新的试剂，HF-ME有效且定量地除去2 S- p -thiocresol- p甲酚（25：65：5：5，V / v / v / v），而没有可检测到的副反应。

  DOI：

  10.1039/c39820000896

文献信息

• [EN] COMPSTATIN ANALOGUES AND THEIR MEDICAL USES<br/>[FR] ANALOGUES DE COMPSTATINE ET LEURS UTILISATIONS MÉDICALES
  申请人：ZP SPV 3 K/S

  公开号：WO2021037942A1

  公开（公告）日：2021-03-04

  Compstatin analogues having improved binding and complement-inhibiting activity as compared to the 13 amino acid compstatin peptide (ICWQDWGHHRCT (cyclic C2-C12)) are described, in particular compstatin analogues that additionally possess useful physicochemical properties. The analogues have a thioether bond rather than a disulfide bond between the side chains of the residues corresponding to cysteines 2 and 12 of compstatin which may increase stability. The analogues may also have an isoleucine residue at position 3 in place of the wild type valine residue, which provides compstatin peptides with improved binding and complement-inhibiting activity and also enables the introduction of other modifications, for example modifications that are capable of increasing solubility, such as the introduction of charged or polar amino acids at position 9 and/or the introduction of N- and/or C-terminal sequences.

  描述了与13氨基酸compstatin肽（ICWQDWGHHRCT（环C2-C12））相比具有改进结合和抑制补体活性的Compstatin类似物，特别是还具有有用的物理化学性质的Compstatin类似物。这些类似物在与compstatin的半胱氨酸2和12号残基相对应的侧链之间具有硫醚键而不是二硫键，这可能增加稳定性。这些类似物还可能在位置3处具有异亮氨酸残基，取代野生型缬氨酸残基，这为compstatin肽提供了改进的结合和抑制补体活性，并且还能引入其他修饰，例如能够增加溶解度的修饰，比如在位置9处引入带电或极性氨基酸以及N-和/或C-末端序列的引入。
• [EN] COMPSTATIN ANALOGS WITH IMPROVED POTENCY AND PHARMACOKINETIC PROPERTIES<br/>[FR] ANALOGUES DE COMPSTATINE DE PUISSANCE ET DE PROPRIÉTÉS PHARMACOCINÉTIQUES AMÉLIORÉES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2015142701A1

  公开（公告）日：2015-09-24

  Compounds comprising peptides capable of binding C3 protein and inhibiting complement activation are disclosed. The compounds include a modified compstatin peptide or analog thereof, comprising an added N-terminal component that improves (1) the binding affinity of the peptide to C3, C3b or C3c and/or (2) the plasma stability and/or plasma residence time of the peptide, as compared with an unmodified compstatin peptide under equivalent conditions. Methods of improving the C3 binding of compstatin or compstatin analogs are also disclosed, as well as methods of designing compstatin analogs with improved C3 binding.

  本发明涉及包含能够结合C3蛋白并抑制补体激活的肽的化合物。这些化合物包括一种经过修改的compstatin肽或其类似物，其中包括一个添加的N-末端组分，该组分改善了肽与C3、C3b或C3c的结合亲和力和/或与未经修改的compstatin肽在等效条件下相比的血浆稳定性和/或血浆停留时间。还公开了改善compstatin或compstatin类似物的C3结合的方法，以及设计具有改善C3结合的compstatin类似物的方法。
• Monomethylvaline Compounds Having Phenylalanine Side-Chain Replacements at the C-Terminus
  申请人：Doronina Svetlana O.

  公开号：US20090018086A1

  公开（公告）日：2009-01-15

  Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) are provided having C-terminal phenylalanine residue side chain replacements or modifications which are provided alone or attached to ligands through various linkers. The related conjugates can target specific cell types to provide therapeutic benefit.

  提供了MeVal-Val-Dil-Dap-Phe（MMAF）的Auristatin肽类类似物，其中包括C-末端苯丙氨酸残基侧链替换或修饰，这些类似物可以单独提供或通过各种连接剂连接到配体上。相关的结合物可以针对特定细胞类型，提供治疗效果。
• MONOMETHYLVALINE COMPOUNDS HAVING PHENYLALANINE SIDE-CHAIN MODIFICATIONS AT THE C-TERMINUS
  申请人：Seattle Genetics, Inc.

  公开号：US20130123465A1

  公开（公告）日：2013-05-16

  Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) are provided having C-terminal phenylalanine residue side chain replacements or modifications which are provided alone or attached to ligands through various linkers. The related conjugates can target specific cell types to provide therapeutic benefit.

  提供了MeVal-Val-Dil-Dap-Phe（MMAF）的Auristatin肽类类似物，其具有C-末端苯丙氨酸残基侧链替换或修饰，可单独提供或通过各种连接剂连接到配体上。相关的结合物可以定向特定的细胞类型，以提供治疗效益。
• LONG-ACTING COMPSTATIN ANALOGS AND USES THEREOF
  申请人：Apellis Pharmaceuticals, Inc.

  公开号：EP4105224A1

  公开（公告）日：2022-12-21

  In some aspects, the present invention provides cell-reactive compstatin analogs and compositions comprising cell-reactive compstatin analogs. In some aspects, the invention further provides methods of using cell-reactive compstatin analogs, e.g., to inhibit complement-mediated damage to a cell, tissue, or organ. In some aspects, the invention provides long-acting compstatin analogs and compositions comprising long-acting compstatin analogs. In some aspects, the invention further provides methods of using long-acting compstatin analogs, e.g., to inhibit complement-mediated damage to a cell, tissue, or organ. In some aspects, the invention provides targeted compstatin analogs and compositions, comprising targeted compstatin analogs. In some aspects, the invention further provides methods of using targeted compstatin analogs, e.g., to inhibit complement-mediated damage to a cell, tissue, or organ.

  在某些方面，本发明提供了细胞反应性复合素类似物和包含细胞反应性复合素类似物的组合物。在某些方面，本发明进一步提供了使用细胞反应性复合司他丁类似物的方法，例如，抑制补体介导的对细胞、组织或器官的损伤。在某些方面，本发明提供了长效的复合素类似物和包含长效复合素类似物的组合物。在某些方面，本发明进一步提供了使用长效抑肽素类似物的方法，例如，抑制补体介导的对细胞、组织或器官的损伤。在某些方面，本发明提供了靶向的复合素类似物和包含靶向复合素类似物的组合物。在某些方面，本发明进一步提供了使用靶向络合素类似物的方法，例如，抑制补体介导的对细胞、组织或器官的损伤。