methyl (S)-2-acetamido-4-(phenylselenyl)butanoate | 1092943-12-8

• 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 (S)-2-acetamido-4-(phenylselenyl)butanoate
• 英文别名: methyl (2S)-2-acetamido-4-phenylselanylbutanoate
• CAS: 1092943-12-8
• 化学式: C₁₃H₁₇NO₃Se
• 分子量: 314.243
• InChiKey: LRIHBISRXHQSAQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-acetamido-4-(phenylselenyl)butanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到(S)-2-acetamido-4-(phenylselenyl)butanoic acid
  参考文献：
  名称：

  Syntheses of the P-Methylase Substrates of the Bialaphos Biosynthetic Pathway

  摘要：

  Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.

  DOI：

  10.1021/ol802269x
• 作为产物：
  描述：

  methyl (S)-2-acetamido-4-bromobutanoate 、 二苯基二硒醚 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以82%的产率得到methyl (S)-2-acetamido-4-(phenylselenyl)butanoate
  参考文献：
  名称：

  Syntheses of the P-Methylase Substrates of the Bialaphos Biosynthetic Pathway

  摘要：

  Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.

  DOI：

  10.1021/ol802269x

文献信息

• Syntheses of the P-Methylase Substrates of the Bialaphos Biosynthetic Pathway
  作者：Youli Xiao、Kent Lee、Pinghua Liu

  DOI：10.1021/ol802269x

  日期：2008.12.18

  Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.