6-[[3,5-Dihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl]methyl]-4-hydroxypyran-2-one | 1110685-29-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 6-[[3,5-Dihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl]methyl]-4-hydroxypyran-2-one
• CAS: 1110685-29-4
• 化学式: C₂₁H₁₆O₇
• 分子量: 380.354
• InChiKey: JEKQNTNFMZMFMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  128.2
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-coumaroyl coenzyme A 、 丙二酰辅酶A-钠盐 在 Aloe arborescens octaketide synthase, wild-type 作用下， 以0.96%的产率得到6-[[3,5-Dihydroxy-2-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl]methyl]-4-hydroxypyran-2-one
  参考文献：
  名称：

  Enzymatic Formation of Unnatural Novel Chalcone, Stilbene, and Benzophenone Scaffolds by Plant Type III Polyketide Synthase

  摘要：

  A C-19 hexaketide stilbene and a C-21 heptaketide chalcone were synthesized by Aloe arborescens octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS). Remarkably, the C21 chalcone-forming activity was dramatically increased in a structure-guided OKS N222G mutant that produces a C-20 decaketide SEK15 from 10 molecules of malonyl-CoA. The findings suggested further strategies for production of unnatural polyketides by combination of the precursor-directed biosynthesis and the structure-guided engineering of type III PKS.

  DOI：

  10.1021/ol802606w

文献信息

• Enzymatic Formation of Unnatural Novel Chalcone, Stilbene, and Benzophenone Scaffolds by Plant Type III Polyketide Synthase
  作者：She-Po Shi、Kiyofumi Wanibuchi、Hiroyuki Morita、Kohei Endo、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1021/ol802606w

  日期：2009.2.5

  A C-19 hexaketide stilbene and a C-21 heptaketide chalcone were synthesized by Aloe arborescens octaketide synthase (OKS), a plant-specific type III polyketide synthase (PKS). Remarkably, the C21 chalcone-forming activity was dramatically increased in a structure-guided OKS N222G mutant that produces a C-20 decaketide SEK15 from 10 molecules of malonyl-CoA. The findings suggested further strategies for production of unnatural polyketides by combination of the precursor-directed biosynthesis and the structure-guided engineering of type III PKS.