5,5'-二甲基-4,4'-联嘧啶-2,2',6(1H,3H,3'H)-三酮 | 20545-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5,5'-二甲基-4,4'-联嘧啶-2,2',6(1H,3H,3'H)-三酮
• 英文名称: thyminyl-(6-4')-(5'-methyl-1',2'-dihydropyrimidin-2'-one)
• 英文别名: 6-4'-<5'-methylpyrimidin-2'-one>-thymine；6-<5-Methyl-2-oxo-1,2-dihydro-pyrimidyl-(4)>-thymin；5,5'-dimethyl-3H,1'H-[4,4']bipyrimidinyl-2,6,2'-trione；5-methyl-6-(5-methyl-2-oxo-1H-pyrimidin-6-yl)-1H-pyrimidine-2,4-dione
• CAS: 20545-68-0
• 化学式: C₁₀H₁₀N₄O₃
• 分子量: 234.214
• InChiKey: IGTSGPZXQJVUAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  99.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为产物：
  描述：

  thymidilyl(3'-5')thymidine 在 吡啶 、 盐酸 、 氢氟酸 作用下， 以 水 为溶剂， 反应 8.5h， 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

文献信息

• The (5‐4) and (6‐4) Adducts of 1‐Methylthymine and Their Dewar Valence Isomers
  作者：Martin D. Shetlar、Janet Chung

  DOI：10.1111/j.1751-1097.2011.00932.x

  日期：2011.7

  AbstractPrevious studies of the photochemical reaction of 1‐methylthymine (MeT) in frozen aqueous solution have indicated that four cyclobutane type dimers are formed. We have restudied this system and have found that, in addition to cyclobutane dimers, both a (5‐4) adduct and a (6‐4) adduct of MeT are formed in significant amounts. Upon standing in aqueous solution, the (5‐4) adduct is susceptible to reaction to form an isomeric form of the parent adduct, possibly via ring‐opening and closure reactions at C‐6 of the saturated pyrimidine ring component of the adduct. Irradiation of each of these three adducts with UVB light produces a pair of Dewar‐type adducts. The nine products were individually characterized by mass spectrometry, proton NMR spectroscopy and UV spectroscopy. A less comprehensive study showed that irradiation of thymidine in frozen aqueous solution produces a diastereomeric pair of (5‐4) adducts, along with the previously known diastereomeric pair of (6‐4) adducts.
• BRYANT J. D.; LEONARD N. J., J. ORG. CHEM. <JOCE-AH>, 1978, 43, NO 3, 511-516
  作者：BRYANT J. D.、 LEONARD N. J.

  DOI：——

  日期：——
• Measurement of Pyrimidine (6-4) Photoproducts in DNA by a Mild Acidic Hydrolysis-HPLC Fluorescence Detection Assay
  作者：Thierry Douki、Lucienne Voituriez、Jean Cadet

  DOI：10.1021/tx00044a010

  日期：1995.3

  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.