methyl N-((S)-2-((tert-butoxycarbonyl)amino)-3-(3-methyl-3H-diazirin-3-yl)propanoyl)-N-methyl-L-phenylalaninate | 1000770-98-8

• 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: methyl N-((S)-2-((tert-butoxycarbonyl)amino)-3-(3-methyl-3H-diazirin-3-yl)propanoyl)-N-methyl-L-phenylalaninate
• CAS: 1000770-98-8
• 化学式: C₂₁H₃₀N₄O₅
• 分子量: 418.493
• InChiKey: ODQCEYIFIBVCGS-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  109.66
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl N-((S)-2-((tert-butoxycarbonyl)amino)-3-(3-methyl-3H-diazirin-3-yl)propanoyl)-N-methyl-L-phenylalaninate 在 lithium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Photo-Leucine Incorporation Reveals the Target of a Cyclodepsipeptide Inhibitor of Cotranslational Translocation

  摘要：

  Photoaffinity labeling is a powerful tool to identify protein targets of biologically active small molecules, yet is often limited,by the size, chemical properties, and availability of photoreactive groups. We report an improved synthesis of photo-leucine, a diazirine-based photoreactive analogue of leucine, and demonstrate its incorporation into a cyclodepsipepticle inhibitor of cotranslational translocation. Photoaffinity labeling in a crude membrane fraction, followed by "click chemistry" with a rhodamine-azide reporter, enabled the identification of Sec61 alpha, the structural core of the Sec61 translocation channel, as the inhibitor's target.

  DOI：

  10.1021/ja076250y
• 作为产物：
  描述：

  (S)-Boc-photo-leucine 、 N-Alpha-甲基-L-苯丙氨酸-甲酯盐酸盐 在 N-羟基-7-氮杂苯并三氮唑 、 碳酸氢钠 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以60%的产率得到methyl N-((S)-2-((tert-butoxycarbonyl)amino)-3-(3-methyl-3H-diazirin-3-yl)propanoyl)-N-methyl-L-phenylalaninate
  参考文献：
  名称：

  Photo-Leucine Incorporation Reveals the Target of a Cyclodepsipeptide Inhibitor of Cotranslational Translocation

  摘要：

  Photoaffinity labeling is a powerful tool to identify protein targets of biologically active small molecules, yet is often limited,by the size, chemical properties, and availability of photoreactive groups. We report an improved synthesis of photo-leucine, a diazirine-based photoreactive analogue of leucine, and demonstrate its incorporation into a cyclodepsipepticle inhibitor of cotranslational translocation. Photoaffinity labeling in a crude membrane fraction, followed by "click chemistry" with a rhodamine-azide reporter, enabled the identification of Sec61 alpha, the structural core of the Sec61 translocation channel, as the inhibitor's target.

  DOI：

  10.1021/ja076250y