5-benzoyl-2-deoxyribonolactone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzoyl-2-deoxyribonolactone
• 英文别名: [(2R,3S)-3-hydroxy-5-oxooxolan-2-yl]methyl benzoate
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: VFNUXWJHAKEYRQ-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzoyl-2-deoxyribonolactone 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以4.4%的产率得到5'-benzoyl-2'-deoxyribose
  参考文献：
  名称：

  Direct measurement of pyrimidine C6-hydrate stability

  摘要：

  Pyrimidine C6-hydrates are produced via UV-irradiation and undergo dehydration upon standing. The stability of these compounds has a direct bearing on their genotoxicity. The rate constants for elimination from 5 ' -benzyoylated derivatives of 5,6-dihydro-5-hydroxythymidine (6) and 5,6-dihydro-5-hydroxy-2 ' -deoxyuridine (9) were measured directly via HPLC. The rate constants for dehydration increase from pH 6.0 to 8.0. The half-lives for 6 and 9 at pH 7.4 and 37 degreesC are 46.5 and 24.4 h, respectively. Deglycosylation is not observed, even upon heating at 90 degreesC. These observations reinforce proposals that pyrimidine hydrates are sufficiently long-lived that they can exert significant effects on biological systems. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00137-7
• 作为产物：
  描述：

  苯甲酰腈 、 D-(+)-核糖酸-gamma-内酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到5-benzoyl-2-deoxyribonolactone
  参考文献：
  名称：

  Independent Generation and Study of 5,6-Dihydro-2‘-deoxyuridin-6-yl, a Member of the Major Family of Reactive Intermediates Formed in DNA from the Effects of γ-Radiolysis

  摘要：

  Nucleobase radicals are the major family of reactive intermediates formed when nucleic acids are exposed to gamma-radiolysis. Elucidation of their reactivity is complicated by the formation of multiple species randomly throughout the biopolymers. 5,6-Dihydro-2'-deoxyuridin-6-yl (1) was generated upon photolysis (350 nm) of the respective tert-butyl ketone (2). The radical abstracts hydrogen atoms from beta-mercaptoethanol (k = 8.8 +/- 0.5 x 10(6) M-1 s(-1)) and 2,5-dimethyltetrahydrofuran (k = 31 +/- 2.5 M-1 s(-1)). The latter was used as a model for the 2-deoxyribose component of DNA. The major product formed in the presence of O-2 was 6-hydroxy-5,6-dihydro-2'-deoxyuridine (11), which is believed to be formed directly from the peroxy precursor and not via elimination of superoxide. Small amounts of 2-deoxyribonolactone (13) were also formed under aerobic conditions. This product is believed to result from intramolecular hydrogen atom abstraction by the C6-peroxyl radical (14) and suggests that gamma-radiolysis may indirectly result in oxidation of the Cl'-position of nucleotides, despite the inaccessibility of this hydrogen in duplex DNA.

  DOI：

  10.1021/jo034038g

文献信息

• Independent Generation and Study of 5,6-Dihydro-2‘-deoxyuridin-6-yl, a Member of the Major Family of Reactive Intermediates Formed in DNA from the Effects of γ-Radiolysis
  作者：K. Nolan Carter、Marc M. Greenberg

  DOI：10.1021/jo034038g

  日期：2003.5.1

  Nucleobase radicals are the major family of reactive intermediates formed when nucleic acids are exposed to gamma-radiolysis. Elucidation of their reactivity is complicated by the formation of multiple species randomly throughout the biopolymers. 5,6-Dihydro-2'-deoxyuridin-6-yl (1) was generated upon photolysis (350 nm) of the respective tert-butyl ketone (2). The radical abstracts hydrogen atoms from beta-mercaptoethanol (k = 8.8 +/- 0.5 x 10(6) M-1 s(-1)) and 2,5-dimethyltetrahydrofuran (k = 31 +/- 2.5 M-1 s(-1)). The latter was used as a model for the 2-deoxyribose component of DNA. The major product formed in the presence of O-2 was 6-hydroxy-5,6-dihydro-2'-deoxyuridine (11), which is believed to be formed directly from the peroxy precursor and not via elimination of superoxide. Small amounts of 2-deoxyribonolactone (13) were also formed under aerobic conditions. This product is believed to result from intramolecular hydrogen atom abstraction by the C6-peroxyl radical (14) and suggests that gamma-radiolysis may indirectly result in oxidation of the Cl'-position of nucleotides, despite the inaccessibility of this hydrogen in duplex DNA.
• Direct measurement of pyrimidine C6-hydrate stability
  作者：K Nolan Carter

  DOI：10.1016/s0968-0896(01)00137-7

  日期：2001.9

  Pyrimidine C6-hydrates are produced via UV-irradiation and undergo dehydration upon standing. The stability of these compounds has a direct bearing on their genotoxicity. The rate constants for elimination from 5 ' -benzyoylated derivatives of 5,6-dihydro-5-hydroxythymidine (6) and 5,6-dihydro-5-hydroxy-2 ' -deoxyuridine (9) were measured directly via HPLC. The rate constants for dehydration increase from pH 6.0 to 8.0. The half-lives for 6 and 9 at pH 7.4 and 37 degreesC are 46.5 and 24.4 h, respectively. Deglycosylation is not observed, even upon heating at 90 degreesC. These observations reinforce proposals that pyrimidine hydrates are sufficiently long-lived that they can exert significant effects on biological systems. (C) 2001 Elsevier Science Ltd. All rights reserved.