N-(tert-Butoxycarbonyl)-O-(dimethylphosphono)-L-tyrosyl p-nitrobenzyl ester | 92264-96-5

• 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: N-(tert-Butoxycarbonyl)-O-(dimethylphosphono)-L-tyrosyl p-nitrobenzyl ester
• 英文别名: (4-nitrophenyl)methyl (2S)-3-(4-dimethoxyphosphoryloxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 92264-96-5
• 化学式: C₂₃H₂₉N₂O₁₀P
• 分子量: 524.464
• InChiKey: HYPFBZKLJATBEZ-FQEVSTJZSA-N

物化性质

• 沸点：
  625.7±55.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  152.53
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)-O-(dimethylphosphono)-L-tyrosyl p-nitrobenzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 23.0 ℃ 、275.79 kPa 条件下， 反应 3.0h， 以93.4%的产率得到Nα-Boc-O-(二甲基磷酸基)-L-酪氨酸
  参考文献：
  名称：

  Synthesis of a Phosphotyrosine-Containing Peptide Fragment of the Regulatory Domain of pp60c-src

  摘要：

  t-Boc-Tyr(PO(3)Me(2))-OH (4) was ulitized in the synthesis of PheThrSerThrGluProGlnTyr(PO3H2)-GlnProGlyGluAsnLeu (1), a phosphotyrosine-containing peptide fragment of the regulatory domain of pp60(c-src). The protected amino acid 4 was employed during the synthesis of PheThrSerThrGluProGlnTyr(PO(3)Me(2))GlnProGlyGluAsnLeu (5), during which problems involving incomplete incorporation of the Tyr(PO(3)Me(2)) residue, as well as partial demethylation of the dimethylphosphono group and dephoshhorylation during peptide synthesis, were encountered. In addition, an acid-catalyzed backbone rearrangement was encountered involving migration of the phenylalanine acyl group from the nitrogen to the hydroxyl group of the adjacent threonine residue during the deprotection of the phosphate group of 5 with a mixture of trifluoromethanesulfonic acid, trifluoroacetic acid, dimethyl sulfide, and m-cresol (10:50:30:10).

  DOI：

  10.1021/jo00087a025
• 作为产物：
  描述：

  sodium;4-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(4-nitrophenyl)methoxy]-3-oxopropyl]phenolate 生成 N-(tert-Butoxycarbonyl)-O-(dimethylphosphono)-L-tyrosyl p-nitrobenzyl ester
  参考文献：
  名称：

  VALERIO, ROBERT M.;ALEWOOD, PAUL F.;JOHNS, R. B.;KEMP, BRUCE E., INT. J. PEPTIDE AND PROTEIN RES., 33,(1989) N, C. 428-438

  摘要：

  DOI：

文献信息

• Synthesis of protected derivatives of O-phosphotyrosine incorporation in a heptapeptide
  作者：R.M. Valerio、P.F. Alewood、R.B. Johns、B.E. Kemp

  DOI：10.1016/s0040-4039(01)81243-0

  日期：1984.1