(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-phenylpropan-2-yl]-1-[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-(5-sulfamoyl-1H-imidazol-2-yl)propanoyl]pyrrolidine-2-carboxamide | 1360157-24-9

• 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)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-phenylpropan-2-yl]-1-[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-(5-sulfamoyl-1H-imidazol-2-yl)propanoyl]pyrrolidine-2-carboxamide
• CAS: 1360157-24-9
• 化学式: C₂₅H₃₅N₉O₇S
• 分子量: 605.675
• InChiKey: DFKRRAZJMMFFKK-DKIMLUQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  274
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 、 Fmoc-L-丙氨酸 、 Fmoc-L-脯氨酸 、 N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide 、 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,Nbis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)-propanoic acid 在 哌啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以42%的产率得到(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-phenylpropan-2-yl]-1-[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-(5-sulfamoyl-1H-imidazol-2-yl)propanoyl]pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Design and Synthesis of an Fmoc-SPPS-Compatible Amino Acid Building Block Mimicking the Transition State of Phosphohistidine Phosphatase

  摘要：

  The synthesis of a sulfonamide-based transition-state (TS) analogue of enzymatic phosphohistidine dephosphorylation as an amino acid building block is presented, together with the proof-of-concept of its incorporation into peptides. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The peptides are designed as inhibitors of phosphohistidine phosphatase and as a pull-down probe for identification of phosphohistidine phosphatases, respectively.

  DOI：

  10.1021/jo2025702

文献信息

• Design and Synthesis of an Fmoc-SPPS-Compatible Amino Acid Building Block Mimicking the Transition State of Phosphohistidine Phosphatase
  作者：Martijn F. Eerland、Christian Hedberg

  DOI：10.1021/jo2025702

  日期：2012.2.17

  The synthesis of a sulfonamide-based transition-state (TS) analogue of enzymatic phosphohistidine dephosphorylation as an amino acid building block is presented, together with the proof-of-concept of its incorporation into peptides. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The peptides are designed as inhibitors of phosphohistidine phosphatase and as a pull-down probe for identification of phosphohistidine phosphatases, respectively.