N-fluorenylmethyloxycarbonyl-4-pyridylalanine-methyl ester | 1397697-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-fluorenylmethyloxycarbonyl-4-pyridylalanine-methyl ester
• 英文别名: methyl 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-pyridin-4-ylpropanoate
• CAS: 1397697-82-3
• 化学式: C₂₄H₂₂N₂O₄
• 分子量: 402.45
• InChiKey: UNVRFKSAWDFAPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.52
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-fluorenylmethyloxycarbonyl-4-pyridylalanine-methyl ester 在 ammonium hydroxide 、 α-chymotrypsine 、 ammonium acetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以40%的产率得到Fmoc-3-(4-吡啶基)-L-丙氨酸
  参考文献：
  名称：

  Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives

  摘要：

  Enantiomerically pure 2-, 3- or 4-pyridylalanine (pya) and 2-azatyrosine (azatyr) are known to present various biological activities. After incorporation into appropriate peptide sequences, these heterocyclic non natural alpha-amino acids could behave as new substrates or inhibitors of elastase from Pseudomonas aeruginosa. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using alpha-chymotrypsin (alpha-CT) are presented.

  DOI：

  10.1007/s00726-010-0829-3
• 作为产物：
  描述：

  (Z)-2-acetamido-3-(pyridin-4-yl) acrylic acid 在 盐酸 、 三甲基氯硅烷 、 palladium 10% on activated carbon 、 水 、 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 70.0h， 生成 N-fluorenylmethyloxycarbonyl-4-pyridylalanine-methyl ester
  参考文献：
  名称：

  Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives

  摘要：

  Enantiomerically pure 2-, 3- or 4-pyridylalanine (pya) and 2-azatyrosine (azatyr) are known to present various biological activities. After incorporation into appropriate peptide sequences, these heterocyclic non natural alpha-amino acids could behave as new substrates or inhibitors of elastase from Pseudomonas aeruginosa. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using alpha-chymotrypsin (alpha-CT) are presented.

  DOI：

  10.1007/s00726-010-0829-3