NH2<-Val<-Val<-Leu<-Gln<-Fum-Ala-Gly-Phe-OH | 1189038-22-9

• 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: NH2<-Val<-Val<-Leu<-Gln<-Fum-Ala-Gly-Phe-OH
• 英文别名: (2S)-2-[[2-[[(2S)-2-[[(E)-4-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-oxobut-2-enoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoic acid
• CAS: 1189038-22-9
• 化学式: C₃₉H₅₉N₉O₁₁
• 分子量: 829.951
• InChiKey: UAQNNBWXJZUVSA-OMZNPZFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  59
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  327
• 氢给体数：
  10
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  NH2<-Val<-Val<-Leu<-Gln<-Fum-Ala-Gly-Phe-OH 、 三乙胺 在 盐酸 作用下， 以 水 为溶剂， 以311 mg的产率得到(2S)-2-[[2-[[(2S)-2-[[(E)-4-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-oxobut-2-enoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoic acid;N,N-diethylethanamine
  参考文献：
  名称：

  On-Bead Screening of a Combinatorial Fumaric Acid Derived Peptide Library Yields Antiplasmodial Cysteine Protease Inhibitors with Unusual Peptide Sequences

  摘要：

  A new class of cysteine protease inhibitors based oil fumaric acid derived oligopeptides was successfully identified from a high-throughput screening of a solid-phase bound combinatorial library. As target enzymes falcipain and rhodesain were used, which play important roles in the life cycles of the parasites which cause malaria (Plasmodium falciparum) and African sleeping sickness (Trypanosoma brucei rhodesiense). The best inhibitors with unusual amino acid sequences not reported before for this type of enzyme were also fully analyzed in detail in solution. K-i values in the lower micromolar and even nanomolar region were found. Some inhibitors are even active against plasmodia and show good selectivity relative to other enzymes. Also the mechanism of action was studied and could be shown to be irreversible inhibition.

  DOI：

  10.1021/jm900629w
• 作为产物：
  描述：

  L-丙氨酸叔丁酯 、 甘氨酸叔丁酯 、 Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 富马酸叔-丁酯 、 L-苯基丙氨酸叔丁酯 、 Fmoc-L-谷氨酰胺 在 N-甲基吗啉 、 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 NH2<-Val<-Val<-Leu<-Gln<-Fum-Ala-Gly-Phe-OH
  参考文献：
  名称：

  On-Bead Screening of a Combinatorial Fumaric Acid Derived Peptide Library Yields Antiplasmodial Cysteine Protease Inhibitors with Unusual Peptide Sequences

  摘要：

  A new class of cysteine protease inhibitors based oil fumaric acid derived oligopeptides was successfully identified from a high-throughput screening of a solid-phase bound combinatorial library. As target enzymes falcipain and rhodesain were used, which play important roles in the life cycles of the parasites which cause malaria (Plasmodium falciparum) and African sleeping sickness (Trypanosoma brucei rhodesiense). The best inhibitors with unusual amino acid sequences not reported before for this type of enzyme were also fully analyzed in detail in solution. K-i values in the lower micromolar and even nanomolar region were found. Some inhibitors are even active against plasmodia and show good selectivity relative to other enzymes. Also the mechanism of action was studied and could be shown to be irreversible inhibition.

  DOI：

  10.1021/jm900629w