(2S,5S,8S,11S,14S,17S)-17-amino-11-(4-aminobutyl)-14-isobutyl-2-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5,8,19-trimethyl-4,7,10,13-tetraoxo-16-thioxo-3,6,9,12,15-pentaazaicosanoic acid | 1547239-98-4

• 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: (2S,5S,8S,11S,14S,17S)-17-amino-11-(4-aminobutyl)-14-isobutyl-2-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5,8,19-trimethyl-4,7,10,13-tetraoxo-16-thioxo-3,6,9,12,15-pentaazaicosanoic acid
• CAS: 1547239-98-4
• 化学式: C₃₇H₅₇N₇O₉S
• 分子量: 775.967
• InChiKey: FVADTPXVQWCKEG-TZGTVAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  54.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  257.21
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,5S,8S,11S,14S,17S)-17-amino-11-(4-aminobutyl)-14-isobutyl-2-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5,8,19-trimethyl-4,7,10,13-tetraoxo-16-thioxo-3,6,9,12,15-pentaazaicosanoic acid 在 乙二胺四乙酸 、 L-半胱氨酸 、 sodium chloride 、 papain 作用下， 生成 、 (S)-2-((S)-2-((S)-2-aminopropanamido)propanamido)-3-(7-methoxy-2-oxo-2H-chromen-4-yl)propanoic acid
  参考文献：
  名称：

  Thioamide-Based Fluorescent Protease Sensors

  摘要：

  Thioamide quenchers can be paired with compact fluorophores to design "turn-on" fluorescent protease substrates. We have used this method to study a variety of serine-, cysteine-, carboxyl-, and metallo-proteases, including trypsin, chymotrypsin, pepsin, thermolysin, papain, and calpain. Since thioamides quench some fluorophores red-shifted from those naturally occurring in proteins, this technique can be used for real time monitoring of protease activity in crude preparations of virtually any protease. We demonstrate the value of this method in three model applications: (1) characterization of papain enzyme kinetics using rapid-mixing experiments, (2) selective monitoring of cleavage at a single site in a peptide with multiple proteolytic sites, and (3) analysis of the specificity of an inhibitor of calpain in cell lysates.

  DOI：

  10.1021/ja412297x
• 作为产物：
  描述：

  [(1S)-3-甲基-1-[(6-硝基-1H-苯并三唑-1-基)硫酮甲基]丁基]氨基甲酸叔丁酯 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(7-methoxy-2-oxo-2H-chromen-4-yl)propanoic acid 在 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 0.83h， 生成 (2S,5S,8S,11S,14S,17S)-17-amino-11-(4-aminobutyl)-14-isobutyl-2-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-5,8,19-trimethyl-4,7,10,13-tetraoxo-16-thioxo-3,6,9,12,15-pentaazaicosanoic acid
  参考文献：
  名称：

  Thioamide-Based Fluorescent Protease Sensors

  摘要：

  Thioamide quenchers can be paired with compact fluorophores to design "turn-on" fluorescent protease substrates. We have used this method to study a variety of serine-, cysteine-, carboxyl-, and metallo-proteases, including trypsin, chymotrypsin, pepsin, thermolysin, papain, and calpain. Since thioamides quench some fluorophores red-shifted from those naturally occurring in proteins, this technique can be used for real time monitoring of protease activity in crude preparations of virtually any protease. We demonstrate the value of this method in three model applications: (1) characterization of papain enzyme kinetics using rapid-mixing experiments, (2) selective monitoring of cleavage at a single site in a peptide with multiple proteolytic sites, and (3) analysis of the specificity of an inhibitor of calpain in cell lysates.

  DOI：

  10.1021/ja412297x