6-(4-(3-aminophenyl)-2-oxobut-3-en-1-yl)-4-hydroxy-2H-pyran-2-one | 1264066-87-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 6-(4-(3-aminophenyl)-2-oxobut-3-en-1-yl)-4-hydroxy-2H-pyran-2-one
• CAS: 1264066-87-6
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: VZLYIEBNVIEGAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.53
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  m-aminocinnamic acid 、 丙二酰辅酶A-钠盐 在 Saccharomyces cerevisiae strain AH₂₂ (MATA leu2-3 leu2-112 his4-519 can1) (ATCC 38626) 、 4-coumaroyl:CoA-ligase 、 chalcone synthase 作用下， 反应 72.0h， 以< 1 mg的产率得到6-(4-(3-aminophenyl)-2-oxobut-3-en-1-yl)-4-hydroxy-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of non-natural flavanones and dihydrochalcones in metabolically engineered yeast

  摘要：

  Flavonoids are plant phenolic compounds that have many interesting medicinal properties. Therefore, there is interest in the synthesis of non-natural flavonoids as they may possess new or enhanced biological activities. In this study, metabolically engineered Saccharomyces cerevisiae expressing 4-coumaroyl:CoA-ligase (4CL) and chalcone synthase (CHS) was explored as a platform for producing non-natural flavanones and dihydrochalcones. By precursor addition of cinnamic acid analogues to the engineered yeast, numerous non-natural flavanones and dihydrochalcones were formed in vivo. Also, several CHS derailment products were formed. Of the isolated compounds, one flavanone and three derailment products were found to be novel compounds. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.05.017