methyl (2S)-2-amino-3-[4-(3-oxobutanoyl)phenyl]propanoate | 944241-85-4

• 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: methyl (2S)-2-amino-3-[4-(3-oxobutanoyl)phenyl]propanoate
• CAS: 944241-85-4
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: WUABWPPNXSQXRD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-amino-3-[4-(3-oxobutanoyl)phenyl]propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到p-(3-oxobutanoyl)-1-phenylalanine
  参考文献：
  名称：

  Genetic introduction of a diketone-containing amino acid into proteins

  摘要：

  An orthogonal tRNA/aminoacyl-tRNA synthetase pair was evolved that makes possible the site-specific incorporation of an unnatural amino acid bearing a beta-diketone side chain into proteins in Escherichia coli with high translational efficiency and fidelity. Proteins containing this unnatural amino acid can be efficiently and selectively modified with hydroxylamine derivatives of fluorophores and other biophysical probes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.094
• 作为产物：
  描述：

  methyl (S)-3-(4-acetylphenyl)-2-((tert-butoxycarbonyl)amino)propanoate 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 methyl (2S)-2-amino-3-[4-(3-oxobutanoyl)phenyl]propanoate
  参考文献：
  名称：

  Genetic introduction of a diketone-containing amino acid into proteins

  摘要：

  An orthogonal tRNA/aminoacyl-tRNA synthetase pair was evolved that makes possible the site-specific incorporation of an unnatural amino acid bearing a beta-diketone side chain into proteins in Escherichia coli with high translational efficiency and fidelity. Proteins containing this unnatural amino acid can be efficiently and selectively modified with hydroxylamine derivatives of fluorophores and other biophysical probes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.094

文献信息

• US8476411B2
  申请人：——

  公开号：US8476411B2

  公开（公告）日：2013-07-02
• Genetic introduction of a diketone-containing amino acid into proteins
  作者：Huaqiang Zeng、Jianming Xie、Peter G. Schultz

  DOI：10.1016/j.bmcl.2006.07.094

  日期：2006.10

  An orthogonal tRNA/aminoacyl-tRNA synthetase pair was evolved that makes possible the site-specific incorporation of an unnatural amino acid bearing a beta-diketone side chain into proteins in Escherichia coli with high translational efficiency and fidelity. Proteins containing this unnatural amino acid can be efficiently and selectively modified with hydroxylamine derivatives of fluorophores and other biophysical probes. (c) 2006 Elsevier Ltd. All rights reserved.