(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-azido-2,3,5,6-tetrafluorophenyl)propanoic acid

• 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: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-azido-2,3,5,6-tetrafluorophenyl)propanoic acid
• 英文别名: (S)-3-(4-azido-2,3,5,6-tetrafluoro-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid；(2S)-3-(4-azido-2,3,5,6-tetrafluorophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• 化学式: C₂₄H₁₆F₄N₄O₄
• 分子量: 500.409
• InChiKey: LHEGNWCZAFZKRH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-azido-2,3,5,6-tetrafluorophenyl)propanoic acid 在 1,3-丙二硫醇 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.08h， 以96%的产率得到(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-amino-2,3,5,6-tetrafluorophenyl)propanoic acid
  参考文献：
  名称：

  Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in ¹⁹F NMR

  摘要：

  Fluorinated amino acids serve as powerful tools in protein chemistry. We synthesized a series of pare-substituted tetrafluorophenylalanines via the regioselective S-NAr chemistry of the commercially available pentafluorophenylalanine Boc-Z. These novel unnatural amino acids display distinct F-19 NMR signatures, making them powerful tools for analyzing protein-membrane interactions with NMR spectroscopy.

  DOI：

  10.1021/ol203140n
• 作为产物：
  描述：

  α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 sodium hydroxide 、 sodium azide 、 Aspergillus melleus acylase-I 、 水 、 叠氮化四丁基铵 、 lithium bromide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.5h， 生成 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-azido-2,3,5,6-tetrafluorophenyl)propanoic acid
  参考文献：
  名称：

  Synthesis of Photoactive p-Azidotetrafluorophenylalanine Containing Peptide by Solid-Phase Fmoc Methodology

  摘要：

  [GRAPHICS]N-Fmoc-L-p-azidotetrafluorophenylalanine was prepared from achiral starting materials using an acetamidomalonate synthesis and enzymatic resolution. A photoactive peptide containing this fluorinated residue could be assembled using solid-phase Fmoc chemistry.

  DOI：

  10.1021/ol026998f

文献信息

• Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in ¹⁹F NMR
  作者：Luoheng Qin、Christopher Sheridan、Jianmin Gao

  DOI：10.1021/ol203140n

  日期：2012.1.20

  Fluorinated amino acids serve as powerful tools in protein chemistry. We synthesized a series of pare-substituted tetrafluorophenylalanines via the regioselective S-NAr chemistry of the commercially available pentafluorophenylalanine Boc-Z. These novel unnatural amino acids display distinct F-19 NMR signatures, making them powerful tools for analyzing protein-membrane interactions with NMR spectroscopy.
• Synthesis of Photoactive <i>p-</i>Azidotetrafluorophenylalanine Containing Peptide by Solid-Phase Fmoc Methodology
  作者：James E. Redman、M. Reza Ghadiri

  DOI：10.1021/ol026998f

  日期：2002.12.1

  [GRAPHICS]N-Fmoc-L-p-azidotetrafluorophenylalanine was prepared from achiral starting materials using an acetamidomalonate synthesis and enzymatic resolution. A photoactive peptide containing this fluorinated residue could be assembled using solid-phase Fmoc chemistry.