(3R)-N-Fmoc-3-fluoro-L-phenylalanine | 1132645-30-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (3R)-N-Fmoc-3-fluoro-L-phenylalanine
• 英文别名: (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-fluoro-3-phenylpropanoic acid；(2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-fluoro-3-phenylpropanoic acid
• CAS: 1132645-30-7
• 化学式: C₂₄H₂₀FNO₄
• 分子量: 405.426
• InChiKey: GUPFJUGSGFQOJV-YADHBBJMSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  624.6±55.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-N-Fmoc-3-fluoro-L-phenylalanine 、 氨基核苷嘌呤霉素 在 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以78%的产率得到3'-amino-3'-deoxy-3'-[(3''R)-N-Fmoc-3''-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine
  参考文献：
  名称：

  Synthesis of a Fluorine-Substituted Puromycin Derivative for Brønsted Studies of Ribosomal-Catalyzed Peptide Bond Formation

  摘要：

  The mechanism by which the ribosome catalyzes peptide bond formation remains controversial, Here we describe the synthesis of a nucleoside that can be used in Bronsted experiments to assess the transition state of ribosome catalyzed peptide bond formation. This substrate is the nucleoside 3'-amino-3'-deoxy-3'-[(3"R)-3-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine, which was prepared from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. This substrate is active in peptide bond formation on the ribosome and is a useful probe for Bronsted analysis experiments on the ribosome.

  DOI：

  10.1021/jo802611t
• 作为产物：
  描述：

  (3R)-3-fluoro-L-Phe 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以90%的产率得到(3R)-N-Fmoc-3-fluoro-L-phenylalanine
  参考文献：
  名称：

  Synthesis of a Fluorine-Substituted Puromycin Derivative for Brønsted Studies of Ribosomal-Catalyzed Peptide Bond Formation

  摘要：

  The mechanism by which the ribosome catalyzes peptide bond formation remains controversial, Here we describe the synthesis of a nucleoside that can be used in Bronsted experiments to assess the transition state of ribosome catalyzed peptide bond formation. This substrate is the nucleoside 3'-amino-3'-deoxy-3'-[(3"R)-3-fluoro-L-phenylalanyl]-N(6),N(6)-dimethyladenosine, which was prepared from (1R,2R)-2-amino-1-phenylpropane-1,3-diol. This substrate is active in peptide bond formation on the ribosome and is a useful probe for Bronsted analysis experiments on the ribosome.

  DOI：

  10.1021/jo802611t