(S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate | 1360157-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate
• 英文别名: methyl (2S)-3-[4-[bis[(2,4-dimethoxyphenyl)methyl]sulfamoyl]-1-tritylimidazol-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 1360157-23-8
• 化学式: C₅₉H₅₆N₄O₁₀S
• 分子量: 1013.18
• InChiKey: VDZQELIVRWQVBO-MPLRIKRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  74
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate 在 三甲基氢氧化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以86%的产率得到(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,Nbis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)-propanoic acid
  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
• 作为产物：
  描述：

  N,N-bis(2,4-dimethoxybenzyl)-1H-imidazole-4-sulfonamide 在 正丁基锂 、 potassium tert-butylate 、 碘 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.99h， 生成 (S)-methyl-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(N,N-bis(2,4-dimethoxybenzyl)sulfamoyl)-1-trityl-1H-imidazol-2-yl)propanoate
  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.