6-[(2-Benzoyl-3,5-dihydroxyphenyl)methyl]-4-hydroxypyran-2-one | 1145787-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-[(2-Benzoyl-3,5-dihydroxyphenyl)methyl]-4-hydroxypyran-2-one
• 英文别名: 6-[(2-benzoyl-3,5-dihydroxyphenyl)methyl]-4-hydroxypyran-2-one
• CAS: 1145787-73-0
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: ICLWGWYWQNNKSF-UHFFFAOYSA-N

物化性质

• 沸点：
  635.2±55.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-(6-氨基嘌呤-9-基)-2-[[[[3-[2-(2-苯甲酰硫乙基氨基甲酰)乙基氨基甲酰]-3-羟基-2,2-二甲基-丙氧基]-羟基-磷酰]氧基-羟基-磷酰]氧基甲基]-4-羟基-四氢呋喃-3-基]氧基膦酸 、 丙二酰辅酶A-钠盐 在 乙二胺四乙酸 、 OKS 作用下， 反应 12.0h， 以8%的产率得到6-[(2-Benzoyl-3,5-dihydroxyphenyl)methyl]-4-hydroxypyran-2-one
  参考文献：
  名称：

  Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase

  摘要：

  The catalytic potential of octaketicle synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C-16 pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C-22 aromatic octaketides from the C-6-C-2 phenylacetyl starter, as well as a novel C-19 heptaketide benzophenone from the C-6-C-1 benzoyl starter. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.170

文献信息

• Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase
  作者：She-Po Shi、Hiroyuki Morita、Kiyofumi Wanibuchi、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1016/j.tetlet.2009.02.170

  日期：2009.5

  The catalytic potential of octaketicle synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C-16 pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C-22 aromatic octaketides from the C-6-C-2 phenylacetyl starter, as well as a novel C-19 heptaketide benzophenone from the C-6-C-1 benzoyl starter. (C) 2009 Elsevier Ltd. All rights reserved.