(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}phenyl)methaneseleninic acid | 1069018-77-4

• 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: (4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}phenyl)methaneseleninic acid
• 英文别名: [4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenyl]methaneseleninic acid
• CAS: 1069018-77-4
• 化学式: C₁₆H₂₃NO₆Se
• 分子量: 404.322
• InChiKey: CEUSGDKNGCAEAX-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}phenyl)methaneseleninic acid 、 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 以 二氯甲烷 为溶剂， 反应 0.03h， 以82%的产率得到methyl N-(tert-butoxycarbonyl)-S-((4-((S)-2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)benzyl)selanyl)-L-cysteinate
  参考文献：
  名称：

  Seleninate in Place of Phosphate: Irreversible Inhibition of Protein Tyrosine Phosphatases

  摘要：

  A homotyrosine based seleninic acid irreversibly inhibits protein tyrosine phosphatases by forming a covalent selenosulfide linkage with the active site cysteine sulfhydryl specifically. The details of the event are revealed by model synthetic studies and by kinetic, mass spectrometric, and crystallographic characterization.

  DOI：

  10.1021/ja804489m
• 作为产物：
  描述：

  在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 以88%的产率得到(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}phenyl)methaneseleninic acid
  参考文献：
  名称：

  Seleninate in Place of Phosphate: Irreversible Inhibition of Protein Tyrosine Phosphatases

  摘要：

  A homotyrosine based seleninic acid irreversibly inhibits protein tyrosine phosphatases by forming a covalent selenosulfide linkage with the active site cysteine sulfhydryl specifically. The details of the event are revealed by model synthetic studies and by kinetic, mass spectrometric, and crystallographic characterization.

  DOI：

  10.1021/ja804489m

文献信息

• Seleninate in Place of Phosphate: Irreversible Inhibition of Protein Tyrosine Phosphatases
  作者：Mohannad Abdo、Sijiu Liu、Bo Zhou、Chad D. Walls、Li Wu、Spencer Knapp、Zhong-Yin Zhang

  DOI：10.1021/ja804489m

  日期：2008.10.8

  A homotyrosine based seleninic acid irreversibly inhibits protein tyrosine phosphatases by forming a covalent selenosulfide linkage with the active site cysteine sulfhydryl specifically. The details of the event are revealed by model synthetic studies and by kinetic, mass spectrometric, and crystallographic characterization.