N-[(9H-芴-9-基甲氧基)羰基]-O-[双[2-(甲基二苯基硅烷基)乙氧基]磷酰]-L-酪氨酸 | 158817-11-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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
• 中文名称: N-[(9H-芴-9-基甲氧基)羰基]-O-[双[2-(甲基二苯基硅烷基)乙氧基]磷酰]-L-酪氨酸
• 英文名称: N^α-(9-fluorenylmethyloxycarbonyl)-O-phosphono>tyrosine
• 英文别名: (Fmoc-Tyr(PO3(2-(methyldiphenylsilyl)ethyl)2)-OH)；(2S)-3-[4-[bis[2-[methyl(diphenyl)silyl]ethoxy]phosphoryloxy]phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 158817-11-9
• 化学式: C₅₄H₅₄NO₈PSi₂
• 分子量: 932.169
• InChiKey: ULCVFQDEKLBKAQ-MPLRIKRWSA-N

物化性质

• 沸点：
  927.0±65.0 °C(Predicted)
• 密度：
  1.26

计算性质

• 辛醇/水分配系数(LogP)：
  9.53
• 重原子数：
  66
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  bis<2-(methyldiphenylsilyl)ethyl> N,N-diisopropylphosphoramidite 在 四氮唑 、 叔丁基过氧化氢 、 potassium hydrogensulfate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-[(9H-芴-9-基甲氧基)羰基]-O-[双[2-(甲基二苯基硅烷基)乙氧基]磷酰]-L-酪氨酸
  参考文献：
  名称：

  Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis

  摘要：

  Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis. The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined. On the basis of these data, the bis[(methyldiphenylsilyl)ethyl]-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO(3)MDPSE(2))-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides. The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.

  DOI：

  10.1021/jo00101a029

文献信息

• Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis
  作者：Hann-Guang Chao、Michael S. Bernatowicz、Paul D. Reiss、Gary R. Matsueda

  DOI：10.1021/jo00101a029

  日期：1994.11

  Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis. The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined. On the basis of these data, the bis[(methyldiphenylsilyl)ethyl]-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO(3)MDPSE(2))-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides. The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.