(5-hydroxy-5,6-dihydrothyminyl)-(6-4')(5'-methyl-1',2'-dihydropyrimidin-2'-one) | 20545-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (5-hydroxy-5,6-dihydrothyminyl)-(6-4')(5'-methyl-1',2'-dihydropyrimidin-2'-one)
• 英文别名: 5-hydroxy-5,5'-dimethyl-4,5-dihydro-3H,1'(3')H-[4,4']bipyrimidinyl-2,6,2'-trione；(5R)-5-hydroxy-5-methyl-6-(5-methyl-2-oxo-1H-pyrimidin-6-yl)-1,3-diazinane-2,4-dione
• CAS: 20545-93-1；26251-79-6
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: FAIHIWDKQVXTTP-PHUNFMHTSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-hydroxy-5,6-dihydrothyminyl)-(6-4')(5'-methyl-1',2'-dihydropyrimidin-2'-one) 在 盐酸 作用下， 反应 1.5h， 生成 5,5'-二甲基-4,4'-联嘧啶-2,2',6(1H,3H,3'H)-三酮
  参考文献：
  名称：

  Measurement of Pyrimidine (6-4) Photoproducts in DNA by a Mild Acidic Hydrolysis-HPLC Fluorescence Detection Assay

  摘要：

  Pyrimidine (6-4) pyrimidone photoproducts constitute one of the major classes of DNA lesions induced by far-UV irradiation. However, their biological role remains difficult to assess partly because of the lack of a specific and sensitive assay for monitoring their formation in DNA. Here is presented a measurement method based on the release of the (6-4) base adducts from DNA followed by an HPLC separation associated with a sensitive and specific fluorescence detection. The quantitative and mechanistic aspects of the chemical hydrolysis, based on the use of hydrogen fluoride stabilized in pyridine, were investigated, using dinucleoside monophosphate (6-4) photoproducts as model compounds. The final hydrolysis products were isolated and characterized by UV, fluorescence, mass, and H-1 NMR spectroscopies. Application of the assay to far-UV irradiated calf thymus DNA provided information on the sequence effect on the rate of formation of three of the four possible bipyrimidine (6-4) photoproducts.

  DOI：

  10.1021/tx00044a010
• 作为产物：
  描述：

  在 吡啶 、 氢氟酸 作用下， 反应 3.0h， 以90%的产率得到(5-hydroxy-5,6-dihydrothyminyl)-(6-4')(5'-methyl-1',2'-dihydropyrimidin-2'-one)
  参考文献：
  名称：

  Measurement of Pyrimidine (6-4) Photoproducts in DNA by a Mild Acidic Hydrolysis-HPLC Fluorescence Detection Assay

  摘要：

  Pyrimidine (6-4) pyrimidone photoproducts constitute one of the major classes of DNA lesions induced by far-UV irradiation. However, their biological role remains difficult to assess partly because of the lack of a specific and sensitive assay for monitoring their formation in DNA. Here is presented a measurement method based on the release of the (6-4) base adducts from DNA followed by an HPLC separation associated with a sensitive and specific fluorescence detection. The quantitative and mechanistic aspects of the chemical hydrolysis, based on the use of hydrogen fluoride stabilized in pyridine, were investigated, using dinucleoside monophosphate (6-4) photoproducts as model compounds. The final hydrolysis products were isolated and characterized by UV, fluorescence, mass, and H-1 NMR spectroscopies. Application of the assay to far-UV irradiated calf thymus DNA provided information on the sequence effect on the rate of formation of three of the four possible bipyrimidine (6-4) photoproducts.

  DOI：

  10.1021/tx00044a010