Fmoc-Thr(PO3H2)-OH | 883726-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Thr(PO3H2)-OH
• 英文别名: (2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phosphonooxybutanoic acid
• CAS: 883726-90-7
• 化学式: C₁₉H₂₀NO₈P
• 分子量: 421.343
• InChiKey: OKIKUSCYAJQLRR-DIFFPNOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-Thr(PO3H2)-OH 、 乙酸酐 、 Fmoc-L-色氨酸 、 聚甘氨酸 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38%的产率得到Ac-Trp-Asn-Ala-[PThr]-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

文献信息

• Isotope coded affinity tags
  申请人：Bayer HealthCare AG

  公开号：EP1477493A1

  公开（公告）日：2004-11-17

  The invention relates to isotope coded affinity tags for the mass spectrometric analysis of amino acid phosphates, phosphopeptides or phosphoproteins, their use and kits comprising the same.

  这项发明涉及同位素编码亲和标签，用于质谱分析氨基酸磷酸酯、磷酸肽或磷酸蛋白，以及它们的使用和包含相同物质的试剂盒。
• Chemical Pyrophosphorylation of Functionally Diverse Peptides
  作者：Alan M. Marmelstein、Lisa M. Yates、John H. Conway、Dorothea Fiedler

  DOI：10.1021/ja411737c

  日期：2014.1.8

  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.