4-[(1S,2R)-2-(Bis-benzyloxy-thiophosphoryloxy)-1-methylcarbamoyl-propylcarbamoyl]-butyric acid tert-butyl ester | 851983-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(1S,2R)-2-(Bis-benzyloxy-thiophosphoryloxy)-1-methylcarbamoyl-propylcarbamoyl]-butyric acid tert-butyl ester
• CAS: 851983-98-7
• 化学式: C₂₈H₃₉N₂O₇PS
• 分子量: 578.667
• InChiKey: OXCMWDGAYWYCDZ-RLWLMLJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  39.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  112.19
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-[(1S,2R)-2-(Bis-benzyloxy-thiophosphoryloxy)-1-methylcarbamoyl-propylcarbamoyl]-butyric acid tert-butyl ester 在 三甲基溴硅烷 苯硫酚 、 间甲酚 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 5-[[(2S,3R)-3-[hydroxy-[(4-nitrophenyl)methylsulfanyl]-oxidophosphaniumyl]oxy-1-(methylamino)-1-oxobutan-2-yl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  Bio-orthogonal Affinity Purification of Direct Kinase Substrates

  摘要：

  Protein phosphorylation is a major mechanism of post-translational protein modification used to control cellular signaling. A challenge in phosphoproteomics is to identify the direct substrates of each protein kinase. Herein, we describe a chemical strategy for delivery of a bio-orthogonal affinity tag to the substrates of an individual protein kinase. The kinase of interest is engineered to transfer a phosphorothioate moiety to phosphoacceptor hydroxyl groups on direct substrates. In a second nonenzymatic step, the introduced phosphorothioate is alkylated with p-nitrobenzylmesylate (PNBM). Antibodies directed against the alkylated phosphorothioate epitope recognize these labeled substrates, but not alkylation products of other cellular nucleophiles. This strategy is demonstrated with Cdk1/cyclinB substrates using ELISA, western blotting, and immunoprecipitation in the context of whole cell lysates.

  DOI：

  10.1021/ja050727t
• 作为产物：
  描述：

  4-((1S,2R)-2-Hydroxy-1-methylcarbamoyl-propylcarbamoyl)-butyric acid tert-butyl ester 在 四氮唑 、 二硫化二苯乙酰 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 4-[(1S,2R)-2-(Bis-benzyloxy-thiophosphoryloxy)-1-methylcarbamoyl-propylcarbamoyl]-butyric acid tert-butyl ester
  参考文献：
  名称：

  Bio-orthogonal Affinity Purification of Direct Kinase Substrates

  摘要：

  Protein phosphorylation is a major mechanism of post-translational protein modification used to control cellular signaling. A challenge in phosphoproteomics is to identify the direct substrates of each protein kinase. Herein, we describe a chemical strategy for delivery of a bio-orthogonal affinity tag to the substrates of an individual protein kinase. The kinase of interest is engineered to transfer a phosphorothioate moiety to phosphoacceptor hydroxyl groups on direct substrates. In a second nonenzymatic step, the introduced phosphorothioate is alkylated with p-nitrobenzylmesylate (PNBM). Antibodies directed against the alkylated phosphorothioate epitope recognize these labeled substrates, but not alkylation products of other cellular nucleophiles. This strategy is demonstrated with Cdk1/cyclinB substrates using ELISA, western blotting, and immunoprecipitation in the context of whole cell lysates.

  DOI：

  10.1021/ja050727t