(5'S)-5',8-cyclo-2'-deoxyguanosine | 105929-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (5'S)-5',8-cyclo-2'-deoxyguanosine
• 英文别名: (5'S)-8,5'-cyclo-2'-deoxyguanosine；5',8-cyclo-2'-deoxyguanosine；(5'S)-cdGuo；(1R,11S,12S,13S)-5-amino-11,13-dihydroxy-15-oxa-2,4,6,9-tetrazatetracyclo[10.2.1.02,10.03,8]pentadeca-3(8),4,9-trien-7-one
• CAS: 105929-27-9
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: JYCOZDWXEDYCIX-NJKOWUITSA-N

物化性质

• 密度：
  2.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5'S)-5',8-cyclo-2'-deoxyguanosine 在 甲酸 作用下， 生成 、 、
  参考文献：
  名称：

  Stability of N-Glycosidic Bond of (5′S)-8,5′-Cyclo-2′-deoxyguanosine

  摘要：

  8,5'-Cyclopurine deoxynucleosides are unique tandem lesions containing an additional covalent bond between the base and the sugar. These mutagenic and genotoxic lesions are repaired only by nucleotide excision repair. The N-glycosidic (or C1'-N9) bond of 2'-deoxyguanosine (dG) derivatives is usually susceptible to acid hydrolysis, but even after cleavage of this bond of the cyclopurine lesions, the base would remain attached to the sugar. Here, the stability of the N-glycosidic bond and the products formed by formic acid hydrolysis of (5'S)-8,5'-cyclo-2'-deoxyguanosine (S-cdG) were investigated. For comparison, the stability of the N-glycosidic bond of 8,5'-cyclo-2',5'-dideoxyguanosine (ddcdG), 8-methyl-2'-deoxyguanosine (8-Me-dG), 7,8-dihydro-8-oxo-2'-deoxyguanosine (8-Oxo-dG), and dG was also studied. In various acid conditions, S-cdG and ddcdG exhibited similar stability to hydrolysis. Likewise, 8-Me-dG and dG showed comparable stability, but the half-lives of the cyclic dG lesions were at least 5-fold higher than those of dG or 8-Me-dG. NMR studies were carried out to investigate the products formed after the cleavage of the C1'-N9 bond. 2-Deoxyribose generated alpha and beta anomers of deoxyribopyranose and deoxyribopyranose oligomers following acid treatment. S-cdG gave alpha- and beta-deoxyribopyranose linked guanine as the major products, but alpha and beta anomers of deoxyribofuranose linked guanine and other products were also detected. The N-glycosidic bond of 8-Oxo-dG was found exceptionally stable in acid. Computational studies determined that both the protonation of the N7 atom and the rate constant in the bond breaking step control the overall kinetics of hydrolysis, but both varied for the molecules studied indicating a delicate balance between the two steps. Nevertheless, the computational approach successfully predicted the trend observed experimentally. For 8-Oxo-dG, the low pK(a) of O-8 and N3 prevented appreciable protonation, making the free energy for N-glycosidic bond cleavage in the subsequent step very high.

  DOI：

  10.1021/tx300302a
• 作为产物：
  描述：

  8-溴-2'-脱氧鸟苷 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 四丁基锡 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.0h， 生成 (5'S)-5',8-cyclo-2'-deoxyguanosine
  参考文献：
  名称：

  合成（5'S）-和（5'R）-5'，8-环2'-脱氧鸟苷衍生物的自由基级联协议*

  摘要：

  可以适当地调节适当取代的8-溴-2'-脱氧鸟苷与Bu 3 SnH / 2,2'-偶氮二异丁腈（AIBN）的反应，以得到良好的类似5'，8-环-2'-脱氧鸟苷衍生物产生，从而提供了容易获得构成重要DNA损伤的修饰核苷的途径。需要大量过量的AIBN。新的C5'–C8键的创建是一种非链自由基级联协议。

  DOI：

  10.1071/ch12494