(E)-4-(4-methoxybenzylamino)-4-oxobut-2-enoic acid | 1207172-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4-(4-methoxybenzylamino)-4-oxobut-2-enoic acid
• 英文别名: (E)-4-[(4-methoxyphenyl)methylamino]-4-oxobut-2-enoic acid
• CAS: 1207172-73-3
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD08898707
• 分子量: 235.24
• InChiKey: WPUCZNLYVFBPAH-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-methoxybenzylamino)-4-oxobut-2-enoic acid 、 Boc-L-Dap-L-Val-O-t-Bu 在 benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(S)-tert-butyl 2-((S)-2-(tert-butoxycarbonylamino)-3-((E)-4-(4-methoxybenzylamino)-4-oxobut-2-enamido)propanamido)-3-methylbutanoate
  参考文献：
  名称：

  Dapdiamides, Tripeptide Antibiotics Formed by Unconventional Amide Ligases

  摘要：

  Construction of a genomic DNA library from Pantoea agglomerans strain CU0119 and screening against the plant pathogen Erwinia amylovora yielded a new family of antibiotics, dapdiamides A-E (1-5). The structures were established through 2D-NMR experiments and mass spectrometry, as well as the synthesis of dapdiamide A (1). Transposon mutagenesis of the active cosmid allowed identification of the biosynthetic gene cluster. The dapdiamide family's promiscuous biosynthetic pathway contains two unconventional amide ligases that are predicted to couple its constituent monomers.

  DOI：

  10.1021/np900685z
• 作为产物：
  描述：

  ethyl (E)-4-[(4-methoxybenzyl)amino]-4-oxobut-2-enoate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以3.66 g的产率得到(E)-4-(4-methoxybenzylamino)-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Dapdiamides, Tripeptide Antibiotics Formed by Unconventional Amide Ligases

  摘要：

  Construction of a genomic DNA library from Pantoea agglomerans strain CU0119 and screening against the plant pathogen Erwinia amylovora yielded a new family of antibiotics, dapdiamides A-E (1-5). The structures were established through 2D-NMR experiments and mass spectrometry, as well as the synthesis of dapdiamide A (1). Transposon mutagenesis of the active cosmid allowed identification of the biosynthetic gene cluster. The dapdiamide family's promiscuous biosynthetic pathway contains two unconventional amide ligases that are predicted to couple its constituent monomers.

  DOI：

  10.1021/np900685z

文献信息

• Dapdiamides, Tripeptide Antibiotics Formed by Unconventional Amide Ligases
  作者：Jessica Dawlaty、Xiaorong Zhang、Michael A. Fischbach、Jon Clardy

  DOI：10.1021/np900685z

  日期：2010.3.26

  Construction of a genomic DNA library from Pantoea agglomerans strain CU0119 and screening against the plant pathogen Erwinia amylovora yielded a new family of antibiotics, dapdiamides A-E (1-5). The structures were established through 2D-NMR experiments and mass spectrometry, as well as the synthesis of dapdiamide A (1). Transposon mutagenesis of the active cosmid allowed identification of the biosynthetic gene cluster. The dapdiamide family's promiscuous biosynthetic pathway contains two unconventional amide ligases that are predicted to couple its constituent monomers.