N-propiolyl-Ile-Ile-OMe | 1252800-22-8

• 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
• 英文名称: N-propiolyl-Ile-Ile-OMe
• CAS: 1252800-22-8
• 化学式: C₁₆H₂₆N₂O₄
• 分子量: 310.393
• InChiKey: MFAMNIGNIZQGHV-IMIFBBOLSA-N

反应信息

• 作为反应物：
  描述：

  N-propiolyl-Ile-Ile-OMe 、 5,10,15,20-tetrakis(3-azidophenyl)porphyrin 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以99%的产率得到
  参考文献：
  名称：

  Facile synthesis of peptide–porphyrin conjugates: Towards artificial catalase

  摘要：

  A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl) porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl) porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase-and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.018
• 作为产物：
  描述：

  L-Ile-L-Ile-OMe 、 丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 N-propiolyl-Ile-Ile-OMe
  参考文献：
  名称：

  Facile synthesis of peptide–porphyrin conjugates: Towards artificial catalase

  摘要：

  A facile synthetic method for peptide-porphyrin conjugates containing four peptide units on one porphyrin was developed using chemoselective reactions. The key building blocks, 5,10,15,20-tetrakis(3-azidophenyl) porphyrin 1 and 5,10,15,20-tetrakis(5-azido-3-pyridyl) porphyrin 2, were efficiently synthesized and used as substrates for two well-known chemoselective reactions, traceless Staudinger ligation and copper-catalyzed azide alkyne cycloaddition (so-called click chemistry). Both reactions gave the desired compounds, and click chemistry was superior for our purpose. To confirm the value of the established methodology, nine peptide-porphyrin conjugates were synthesized, and their catalase-and peroxidase-like activity in water was evaluated. Our synthetic strategy is expected to be valuable for the preparation of artificial heme protein models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.018