Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-((5R,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 793684-21-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-((5R,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS: 793684-21-6
• 化学式: C₂₆H₃₂N₇O₁₂PS
• 分子量: 697.62
• InChiKey: XIVJZSFKWBWDJW-RNJYWACESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  273.91
• 氢给体数：
  7.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-((5R,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 在 水 作用下， 反应 0.33h， 生成 、 Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-((S)-5-hydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 、 、 Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-((5S,6R)-5,6-dihydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
  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：

  在 4,5-二氰基咪唑 、 氨 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.67h， 生成 Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-((5R,6R)-5-hydroxy-5-methyl-2,4-dioxo-6-phenylsulfanyl-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  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