O,O-(5S,6S)-trans-(-)-5-bromo-6-hydroxy-5,6-dihydrothymidine-3',5'-diyldiacetate | 43179-41-5

• 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: O,O-(5S,6S)-trans-(-)-5-bromo-6-hydroxy-5,6-dihydrothymidine-3',5'-diyldiacetate
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-[(5S,6S)-5-bromo-6-hydroxy-5-methyl-2,4-dioxo-1,3-diazinan-1-yl]oxolan-2-yl]methyl acetate
• CAS: 43179-41-5
• 化学式: C₁₄H₁₉BrN₂O₈
• 分子量: 423.217
• InChiKey: JHRCUFUUKOYNIP-KVEPIYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O,O-(5S,6S)-trans-(-)-5-bromo-6-hydroxy-5,6-dihydrothymidine-3',5'-diyldiacetate 在 吡啶 、 氨 、 zinc(II) oxide 作用下， 以 甲醇 、 苯 为溶剂， 生成 (5S,6S)-cis-5-hydroxy-6-phenylthio-5,6-dihydrothymidine
  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 水 、 溴 作用下， 反应 0.25h， 以62.3%的产率得到O,O-(5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine-3',5'-diyldiacetate
  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

文献信息

• Harayama, Takashi; Yanada, Reiko; Tanaka, Mihoko, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2555 - 2562
  作者：Harayama, Takashi、Yanada, Reiko、Tanaka, Mihoko、Taga, Tooru、Machida, Katsunosuke、et al.

  DOI：——

  日期：——
• HARAYAMA, TAKASHI;YANADA, REIKO;TANAKA, MIHOKO;TAGA, TOORU;MACHIDA, KATSU+, J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 9, C. 2555-2562
  作者：HARAYAMA, TAKASHI、YANADA, REIKO、TANAKA, MIHOKO、TAGA, TOORU、MACHIDA, KATSU+

  DOI：——

  日期：——