(E)-4-hydroxy-6-(5-(4-hydroxyphenyl)-3-oxopent-4-en-2-yl)-3,5-dimethyl-2H-pyrone

• 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: (E)-4-hydroxy-6-(5-(4-hydroxyphenyl)-3-oxopent-4-en-2-yl)-3,5-dimethyl-2H-pyrone
• 英文别名: 4-hydroxy-6-[(E)-5-(4-hydroxyphenyl)-3-oxopent-4-en-2-yl]-3,5-dimethylpyran-2-one
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: HLFQCXHADDCQLV-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-2-[[羟基-[羟基-[3-羟基-3-[2-[2-[(E)-3-(4-羟基苯基)丙-2-烯酰基]硫基乙基氨基甲酰]乙基氨基甲酰]-2,2-二甲基-丙氧基]磷酰]氧基-磷酰]氧基甲基]四氢呋喃-3-基]氧基膦酸 、 甲基丙二酰-辅酶A 在 recombinant type III polyketide synthase from Aquilaria sinensis 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 生成 (E)-4-hydroxy-6-(4-hydroxystyryl)-3,5-dimethyl-2H-pyrone 、 (E)-4-hydroxy-6-(5-(4-hydroxyphenyl)-3-oxopent-4-en-2-yl)-3,5-dimethyl-2H-pyrone
  参考文献：
  名称：

  Rapid preparation of (methyl)malonyl coenzyme A and enzymatic formation of unusual polyketides by type III polyketide synthase from Aquilaria sinensis

  摘要：

  (Methyl) malonyl coenzyme A was rapidly and effectively synthesized by a two-step procedure involving preparation of N-hydroxysuccinimidyl (methyl) malonate from (methyl) Meldrum's acid, and followed by transesterification with coenzyme A. The synthesized (methyl) malonyl coenzyme A could be well accepted and assembled to 4-hydroxy phenylpropionyl coenzyme A by type III polyketide synthase from Aquilaria sinensis to produce dihydrochalcone and 4-hydroxy-3,5-dimethyl-6-(4-hydroxyphenethyl)-2H-pyrone as well as 4-hydroxy-3,5-dimethyl-6-(5-(4-hydroxyphenyl)-3-oxopentan-2-yl)-2H-pyrone. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.045

文献信息

• Enzymatic Formation of an Unnatural C₆−C₅ Aromatic Polyketide by Plant Type III Polyketide Synthases
  作者：Ikuro Abe、Yusuke Takahashi、Hiroshi Noguchi

  DOI：10.1021/ol0201409

  日期：2002.10.1

  [reaction: see text] Substrate specificities of plant polyketide synthases (PKSs) were investigated using analogues of malonyl-CoA, the extension unit of the polyketide chain elongation reactions. When incubated with methylmalonyl-CoA and 4-coumaroyl-CoA, plant PKSs (chalcone synthase from Scutellaria baicalensis, stilbene synthase from Arachis hypogaea, and benzalacetone synthase from Rheum palmatum) afforded

  [反应：见正文]使用丙二酰-CoA的类似物（聚酮化合物链延长反应的延伸单元）研究了植物聚酮化合物合酶（PKS）的底物特异性。与甲基丙二酰辅酶A和4-香豆酰辅酶A一起孵育时，植物PKSs（黄S的查耳酮合酶，花生小穗的二苯乙烯合酶和棕榈大黄的苯丙丙酮合酶）提供了非天然的C（6）-C（5）芳香族聚缩酮， 1-（4-羟苯基）戊-1-烯-3-酮，通过两个底物的一步脱羧缩合反应形成。相反，该酶不接受琥珀酰-CoA作为底物。