Ac-Trp-His-Asn-Ala-[PSer]-Ala-Asn-Gly-CONH2 | 1522124-72-6

• 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: Ac-Trp-His-Asn-Ala-[PSer]-Ala-Asn-Gly-CONH2
• CAS: 1522124-72-6
• 化学式: C₃₈H₅₃N₁₄O₁₅P
• 分子量: 976.897
• InChiKey: OQGWXIQQZAOFFT-PIFSVREYSA-N

物化性质

• 密度：
  1.485±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.41
• 重原子数：
  68.0
• 可旋转键数：
  27.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  473.3
• 氢给体数：
  15.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Ac-Trp-His-Asn-Ala-[PSer]-Ala-Asn-Gly-CONH2 、 lithium benzyl (1H-imidazol-1-yl)phosphonate 在 zinc(II) chloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.5h， 生成 Ac-Trp-His-Asn-Ala-[monobenzylpyroPSer]-Ala-Asn-Gly-CONH2
  参考文献：
  名称：

  Chemical Pyrophosphorylation of Functionally Diverse Peptides

  摘要：

  A highly selective and convenient method for the synthesis of pyrophosphopeptides in solution is reported. The remarkable compatibility with functional groups (alcohol, thiol, amine, carboxylic acid) in the peptide substrates suggests that the intrinsic nucleophilicity of the phosphoserine residue is much higher than previously appreciated. Because the methodology operates in polar solvents, including water, a broad range of pyrophosphopeptides can be accessed. We envision these peptides will find widespread applications in the development of mass spectrometry and antibody-based detection methods for pyrophosphoproteins.

  DOI：

  10.1021/ja411737c
• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 乙酸酐 、 Fmoc-L-色氨酸 、 Fmoc-L-天冬酰胺 、 N-芴甲氧羰基-L-组氨酸 、 聚甘氨酸 、 Fmoc-O-磷酰-L-丝氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以33%的产率得到Ac-Trp-His-Asn-Ala-[PSer]-Ala-Asn-Gly-CONH2
  参考文献：
  名称：

  Chemical Pyrophosphorylation of Functionally Diverse Peptides

  摘要：

  A highly selective and convenient method for the synthesis of pyrophosphopeptides in solution is reported. The remarkable compatibility with functional groups (alcohol, thiol, amine, carboxylic acid) in the peptide substrates suggests that the intrinsic nucleophilicity of the phosphoserine residue is much higher than previously appreciated. Because the methodology operates in polar solvents, including water, a broad range of pyrophosphopeptides can be accessed. We envision these peptides will find widespread applications in the development of mass spectrometry and antibody-based detection methods for pyrophosphoproteins.

  DOI：

  10.1021/ja411737c