N_α-(isovaleroyl)-D-His-L-Ile-L-Val-L-Pro-NH₂ | 1438891-11-2

• 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_α-(isovaleroyl)-D-His-L-Ile-L-Val-L-Pro-NH₂
• 英文别名: isovaleryl-D-His-Ile-Val-Pro-NH2；(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2R)-3-(1H-imidazol-5-yl)-2-(3-methylbutanoylamino)propanoyl]amino]-3-methylpentanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carboxamide
• CAS: 1438891-11-2
• 化学式: C₂₇H₄₅N₇O₅
• 分子量: 547.698
• InChiKey: OXYBUXPJWVHMGX-RTEGGPEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  179
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N(im)-trityl-D-histidine 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 三异丙基硅烷 、 1-羟基苯并三唑 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 N_α-(isovaleroyl)-D-His-L-Ile-L-Val-L-Pro-NH₂
  参考文献：
  名称：

  Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads

  摘要：

  We report not only the convergent total synthesis of falcitidin, a natural inhibitor of falcipain-2 from myxobacterium Chitinophaga, but also its diversification into a new antimalarial class of N-acyl tetrapeptides (Acyl-His-Ile-Val-Pro-NH2). Despite the lack of whole-cell activity of falcitidin itself, our study led to the identification of a trifluoromethyl (CF3) analogue displaying sub-micromolar IC50 activity against Plasmodium falciparum 3D7 in a standard blood-cell assay, but only when N-tritylated on its histidine (imidazole) residue. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.008

文献信息

• Identification, Characterization, and Synthesis of Natural Parasitic Cysteine Protease Inhibitors: Pentacitidins Are More Potent Falcitidin Analogues
  作者：Stephan Brinkmann、Sandra Semmler、Christian Kersten、Maria A. Patras、Michael Kurz、Natalie Fuchs、Stefan J. Hammerschmidt、Jenny Legac、Peter E. Hammann、Andreas Vilcinskas、Philip J. Rosenthal、Tanja Schirmeister、Armin Bauer、Till F. Schäberle

  DOI：10.1021/acschembio.1c00861

  日期：2022.3.18
• Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads
  作者：Santosh R. Kotturi、Brinda Somanadhan、Jun-Hong Ch’ng、Kevin S.-W. Tan、Mark S. Butler、Martin J. Lear

  DOI：10.1016/j.tetlet.2014.02.008

  日期：2014.3

  We report not only the convergent total synthesis of falcitidin, a natural inhibitor of falcipain-2 from myxobacterium Chitinophaga, but also its diversification into a new antimalarial class of N-acyl tetrapeptides (Acyl-His-Ile-Val-Pro-NH2). Despite the lack of whole-cell activity of falcitidin itself, our study led to the identification of a trifluoromethyl (CF3) analogue displaying sub-micromolar IC50 activity against Plasmodium falciparum 3D7 in a standard blood-cell assay, but only when N-tritylated on its histidine (imidazole) residue. (c) 2014 Elsevier Ltd. All rights reserved.