tert-butyl (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((2-((2,4-dinitrophenyl)amino)ethyl)amino)-5-oxopentanoate | 154036-08-5

• 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: tert-butyl (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((2-((2,4-dinitrophenyl)amino)ethyl)amino)-5-oxopentanoate
• 英文别名: Fmoc-Glu(OtBu)-EDDnp
• CAS: 154036-08-5
• 化学式: C₃₂H₃₅N₅O₉
• 分子量: 633.658
• InChiKey: QMUMBMYUYUCAIB-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  192.04
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((2-((2,4-dinitrophenyl)amino)ethyl)amino)-5-oxopentanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((2-((2,4-dinitrophenyl)amino)ethyl)amino)-5-oxopentanoic acid
  参考文献：
  名称：

  In Silico Design, Synthesis, and Assays of Specific Substrates for Proteinase 3: Influence of Fluorogenic and Charged Groups

  摘要：

  Neutrophil serine proteases are specific regulators of the immune response, and proteinase 3 is a major target antigen in antineutrophil cytoplasmic antibody-associated vasculitis. FRET peptides containing 2-aminobenzoic acid (Abz) and N-(2,4-dinitrophenyl)ethylenediamine (EDDnp) as fluorophore and quencher groups, respectively, have been widely used to probe proteases specificity. Using in silico design followed by enzymatic assays, we show that Abz and EDDnp significantly contribute to substrate hydrolysis by PR3. We also propose a new substrate specific for PR3.

  DOI：

  10.1021/jm401559r
• 作为产物：
  描述：

  Fmoc-O-叔丁基-L-谷氨酸 、 N-(2-氨基乙基)-2,4-二硝基苯胺盐酸盐 在 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 以95%的产率得到tert-butyl (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((2-((2,4-dinitrophenyl)amino)ethyl)amino)-5-oxopentanoate
  参考文献：
  名称：

  In Silico Design, Synthesis, and Assays of Specific Substrates for Proteinase 3: Influence of Fluorogenic and Charged Groups

  摘要：

  Neutrophil serine proteases are specific regulators of the immune response, and proteinase 3 is a major target antigen in antineutrophil cytoplasmic antibody-associated vasculitis. FRET peptides containing 2-aminobenzoic acid (Abz) and N-(2,4-dinitrophenyl)ethylenediamine (EDDnp) as fluorophore and quencher groups, respectively, have been widely used to probe proteases specificity. Using in silico design followed by enzymatic assays, we show that Abz and EDDnp significantly contribute to substrate hydrolysis by PR3. We also propose a new substrate specific for PR3.

  DOI：

  10.1021/jm401559r