(S)-3-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-methyl-butyrylamino}-4-oxo-4-phenyl-butyric acid methyl ester | 863667-31-6

• 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: (S)-3-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-methyl-butyrylamino}-4-oxo-4-phenyl-butyric acid methyl ester
• CAS: 863667-31-6
• 化学式: C₃₅H₅₂N₄O₁₁
• 分子量: 704.818
• InChiKey: YSQIXANKSZLTOW-MGQBIDJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  50.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  212.37
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (S)-3-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-methyl-butyrylamino}-4-oxo-4-phenyl-butyric acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以55%的产率得到(4S)-4-[(2S)-2-(Acetylamino)-3-carboxypropanoyl]amino-5-[(1S)-1-([(1S)-1-(carboxymethyl)-2-oxo-2-phenylethyl]aminocarbonyl)-2-methylpropyl]amino-5-oxopentanoic acid
  参考文献：
  名称：

  Using Peptidic Inhibitors to Systematically Probe the S1‘ Site of Caspase-3 and Caspase-7

  摘要：

  Fifteen ketone-containing peptides were designed, synthesized, and used to probe the effect of substitution at the P1' position on caspase-3 and -7 inhibition. Even with the large bias of Ac-Asp-Glu-Val-Asp at the P4-P1 positions, certain peptides with cyclic functionality in the P1' position show a dramatically reduced ability to inhibit these caspases. Additionally, trends toward isozyme selectivity were also uncovered for particular P1' substituents. The data indicate that substitution in the P1' position can drastically affect both caspase inhibition and selectivity.

  DOI：

  10.1021/ol051287d
• 作为产物：
  描述：

  Ac-Asp(O-t-Bu)-Glu(O-t-Bu)-Val allyl ester 在 吗啉 、 四(三苯基膦)钯 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 (S)-3-{(S)-2-[(S)-2-((S)-2-Acetylamino-3-tert-butoxycarbonyl-propionylamino)-4-tert-butoxycarbonyl-butyrylamino]-3-methyl-butyrylamino}-4-oxo-4-phenyl-butyric acid methyl ester
  参考文献：
  名称：

  Using Peptidic Inhibitors to Systematically Probe the S1‘ Site of Caspase-3 and Caspase-7

  摘要：

  Fifteen ketone-containing peptides were designed, synthesized, and used to probe the effect of substitution at the P1' position on caspase-3 and -7 inhibition. Even with the large bias of Ac-Asp-Glu-Val-Asp at the P4-P1 positions, certain peptides with cyclic functionality in the P1' position show a dramatically reduced ability to inhibit these caspases. Additionally, trends toward isozyme selectivity were also uncovered for particular P1' substituents. The data indicate that substitution in the P1' position can drastically affect both caspase inhibition and selectivity.

  DOI：

  10.1021/ol051287d