5-benzyl-4,7-dihydroxy-coumarin | 1145787-67-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-benzyl-4,7-dihydroxy-coumarin
• 英文别名: 2H-1-Benzopyran-2-one, 4,7-dihydroxy-5-(phenylmethyl)-；5-benzyl-4,7-dihydroxychromen-2-one
• CAS: 1145787-67-2
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: ZOBYJDSRGUUFEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二酰辅酶A-钠盐 、 [(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-2-[[羟基-[羟基-[3-羟基-2,2-二甲基-3-[2-[2-(2-苯基乙酰基)硫基乙基氨基甲酰]乙基氨基甲酰]丙氧基]磷酰]氧基-磷酰]氧基甲基]四氢呋喃-3-基]氧基膦酸 在 乙二胺四乙酸 、 OKS 作用下， 反应 12.0h， 以22%的产率得到5-benzyl-4,7-dihydroxy-coumarin
  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.