[(2R,3S,5R)-3-acetyloxy-5-[(5S,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-1,3-diazinan-1-yl]oxolan-2-yl]methyl acetate | 793684-09-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,5R)-3-acetyloxy-5-[(5S,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-1,3-diazinan-1-yl]oxolan-2-yl]methyl acetate
• CAS: 793684-09-0
• 化学式: C₂₀H₂₄N₂O₈S
• 分子量: 452.485
• InChiKey: YJQIFGLPBIOJRP-QQRQNBNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-[(5S,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-1,3-diazinan-1-yl]oxolan-2-yl]methyl acetate 在 4,5-二氰基咪唑 、 氨 、 水 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Independent Generation of the 5-Hydroxy-5,6-dihydrothymidin-6-yl Radical and Its Reactivity in Dinucleoside Monophosphates

  摘要：

  Hydroxyl radical is a major reactive oxygen species produced by gamma-radiolysis of water or Fenton reaction. It attacks pyrimidine bases and gives the 5-hydroxy-5,6-dihydropyrimidin-6-yl radical as the major product. Here we report the synthesis of all four stereoisomers of 5-hydroxy-6-phenylthio-5,6-dihydrothymidine (T*), which, upon 254 nm UV irradiation, give rise to the 5-hydroxy-5,6-dihydrothymidin-6-yl radical (1). We also incorporated the photolabile radical precursors into dinucleoside monophosphates d(GT*) and d(TT*) and characterized major products resulting from the 254-nm irradiation of these dinucleoside monophosphates. Our results showed that, under anaerobic conditions, the most abundant product emanating from the 254-nm irradiation of d(GT*) and d(TT*) is an abasic site lesion. Products with the thymine portion being modified to thymine glycol and 5-hydroxy-5,6-dihydrothymine were also observed. In addition, we demonstrated that radical I can attack the C8 carbon atom of its 5' neighboring guanine and give rise to a novel cross-link lesion. Moreover, LC-MS/MS results showed that gamma-radiation of d(GT) under anaerobic condition yielded the same type of cross-link lesions.

  DOI：

  10.1021/ja048492t
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 吡啶 、 水 、 溴 、 zinc(II) oxide 作用下， 以 苯 为溶剂， 反应 0.25h， 生成 [(2R,3S,5R)-3-acetyloxy-5-[(5S,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-1,3-diazinan-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Independent Generation of the 5-Hydroxy-5,6-dihydrothymidin-6-yl Radical and Its Reactivity in Dinucleoside Monophosphates

  摘要：

  Hydroxyl radical is a major reactive oxygen species produced by gamma-radiolysis of water or Fenton reaction. It attacks pyrimidine bases and gives the 5-hydroxy-5,6-dihydropyrimidin-6-yl radical as the major product. Here we report the synthesis of all four stereoisomers of 5-hydroxy-6-phenylthio-5,6-dihydrothymidine (T*), which, upon 254 nm UV irradiation, give rise to the 5-hydroxy-5,6-dihydrothymidin-6-yl radical (1). We also incorporated the photolabile radical precursors into dinucleoside monophosphates d(GT*) and d(TT*) and characterized major products resulting from the 254-nm irradiation of these dinucleoside monophosphates. Our results showed that, under anaerobic conditions, the most abundant product emanating from the 254-nm irradiation of d(GT*) and d(TT*) is an abasic site lesion. Products with the thymine portion being modified to thymine glycol and 5-hydroxy-5,6-dihydrothymine were also observed. In addition, we demonstrated that radical I can attack the C8 carbon atom of its 5' neighboring guanine and give rise to a novel cross-link lesion. Moreover, LC-MS/MS results showed that gamma-radiation of d(GT) under anaerobic condition yielded the same type of cross-link lesions.

  DOI：

  10.1021/ja048492t