Abz-Val-Ala-Asp-Nva-Ala-Asp-Tyr-Gln-EDDnp | 1538576-34-9

• 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: Abz-Val-Ala-Asp-Nva-Ala-Asp-Tyr-Gln-EDDnp
• 英文别名: 2-amino-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-azaniumyl-1-[2-(2,4-dinitroanilino)ethylamino]-1,5-dioxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]benzenecarboximidate
• CAS: 1538576-34-9
• 化学式: C₅₃H₇₀N₁₄O₁₉
• 分子量: 1207.22
• InChiKey: DVEPRIKDIMGMCK-WMRGOAQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  86
• 可旋转键数：
  33
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  530
• 氢给体数：
  15
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  Abz-Val-Ala-Asp-Nva-Ala-Asp-Tyr-Gln-EDDnp 在 neutrophil serine proteinase 3 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 AbzVADnV
  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-L-丙氨酸 、 (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((2-((2,4-dinitrophenyl)amino)ethyl)amino)-5-oxopentanoic acid 、 Fmoc-L-酪氨酸 、 Fmoc-L-天冬氨酸 beta-叔丁酯 、 邻氨基苯甲酸 、 Fmoc-L-谷氨酰胺 、 Fmoc-L-正缬氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 Abz-Val-Ala-Asp-Nva-Ala-Asp-Tyr-Gln-EDDnp
  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

文献信息

• In Silico Design, Synthesis, and Assays of Specific Substrates for Proteinase 3: Influence of Fluorogenic and Charged Groups
  作者：Shailesh Narawane、Adnan Budnjo、Cédric Grauffel、Bengt Erik Haug、Nathalie Reuter

  DOI：10.1021/jm401559r

  日期：2014.2.13

  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.