5-(氢过氧基甲基)-1-[(2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶-2,4-二酮 | 38716-10-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-(氢过氧基甲基)-1-[(2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶-2,4-二酮
• 英文名称: 5-(hydroperoxymethyl)-2'-deoxyuridine
• 英文别名: 5-Hydroperoxymethyl-2'-deoxyuridine；5-(hydroperoxymethyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 38716-10-8
• 化学式: C₁₀H₁₄N₂O₇
• 分子量: 274.23
• InChiKey: STXZSCOOCRDNCN-XLPZGREQSA-N

物化性质

• 密度：
  1.596±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (+)-trans-(5R,6R)-5-bromo-6-hydroxy-5,6-dihydrothymidine 在 双氧水 作用下， 以 水 为溶剂， 反应 17.5h， 生成 5-(氢过氧基甲基)-1-[(2R,4S,5R)-4-羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶-2,4-二酮
  参考文献：
  名称：

  无氧水溶液中 2,2,6,6-四甲基-1,4-哌啶酮-N-氧基与胸苷的辐射诱导结合。加合物的分离和表征

  摘要：

  已在 2,2,6,6-四甲基-1,4-哌啶酮-N-氧基 (TAN)（一种众所周知的放射增敏剂）存在下对脱气的胸苷水溶液进行稳态 γ-辐射分解。胸苷的八种主要辐射诱导的 TAN 加成产物已被分离出来，并通过 1H 和 13C nmr、cd 和快速原子轰击质谱测量进行表征。

  DOI：

  10.1139/v85-002

文献信息

• Peroxy Radical Oxidation of Thymidine
  作者：Michela Martini、John Termini

  DOI：10.1021/tx960154l

  日期：1997.2.1

  in the production of DNA base damage and the mutagenic process. We report here on the reaction products formed by peroxy radical with thymidine, major target of oxidative base damage. ROO reacts with thymine to yield predominantly 5-Me oxidation products. The highly mutagenic 5-(hydroperoxymethyl)-2'-deoxyuridine, 5-formyl-2'-deoxyuridine, and 5-(hydroxymethyl)-2'-deoxyuridine are produced by peroxy

  过氧自由基（ROO）在涉及DNA损伤的活性氧物种中是独特的，因为它具有极长的半衰期（几秒钟的数量级），并且据预测在反应中相对于其他化合物具有相对较高的化学选择性。自由基中间体。然而，尚未出现有关ROO与碱基，核苷或DNA反应的产物研究，因此无法就其可能参与DNA碱基破坏的产生和诱变过程做出有意义的预测。我们在这里报告过氧自由基与胸苷（氧化性碱破坏的主要靶标）形成的反应产物。ROO与胸腺嘧啶反应，主要生成5-Me氧化产物。高度致突变的5-（氢过氧甲基）-2'-脱氧尿苷，5-甲酰基-2'-脱氧尿苷和5-（羟甲基）-2' -过氧尿苷是通过过氧自由基氧化产生的。相反，5Me氧化产物是胸苷被OH氧化的次要产物，通过加成5,6双键，主要生成饱和衍生物。提出了通过过氧自由基形成胸腺嘧啶的基础氧化产物的可行机理方案。如游离碱释放所指示，还发现在脱氧核糖部分上的连接导致氧化脱嘧啶作用。如使用质粒切口测定所证
• Mild Generation of 5-(2‘-Deoxyuridinyl)methyl Radical from a Phenyl Selenide Precursor
  作者：In Seok Hong、Marc M. Greenberg

  DOI：10.1021/ol047754t

  日期：2004.12.1

  [reaction: see text] 5-(2'-Deoxyuridinyl)methyl radical (1) resulting from formal hydrogen atom abstraction from the methyl group of thymidine is produced from the respective phenyl selenide precursor (2) via 350 nm photolysis or mild thermolysis (37 degrees C in the presence of glutathione) under aerobic or anaerobic conditions. The mild thermal generation of a nucleoside radical provides an alternative

  [反应：请参见文本]相应的苯基硒化物前体（2）经过350 nm光解或温和热解后，产生了从胸苷甲基中正式氢原子提取而来的5-（2'-Deoxyuridinyl）甲基（1）（在有氧或厌氧条件下，在谷胱甘肽存在下37摄氏度）。核苷自由基的温和生热提供了以前报道的光化学方法的替代方法，这些方法并不总是与核酸相容。
• Thymidine Hydroperoxides: Structural Assignment, Conformational Features, and Thermal Decomposition in Water
  作者：J. R. Wagner、J. E. van Lier、M. Berger、J. Cadet

  DOI：10.1021/ja00085a001

  日期：1994.3

  The primary products of DNA oxidation by free radicals are thymidine hydroperoxides, which include eight diastereomers of 5(6)-hydroxy-6(5)-hydroperoxy-5,6-dihydrothymidine and 5-(hydroperoxymethyl)-2'-deoxyuridine. The hydroperoxides were prepared by trifluoroperacetic acid oxidation of thymidine, which gave the four trans and cis diastereomers of 5-hydroxy-6-hydroperoxy-5,6-dihydrothymidine, and sensitized photooxidation of thymidine with 2-methyl-1,4-naphthoquinone and near-UV light, which gave the four trans and cis diasteromers of 5-hydroperoxy-6-hydroxy-5,6-dihydrothymidine as well as 5-(hydroperoxymethyl)-2'-deoxyuridine. H-1 and C-13 NMR analyses suggested that the pyrimidine ring of thymidine 5,6-hydroxyhydroperoxides adopts four puckered conformations in which the orientations of the C6 hydroxy or hydroperoxy substituents are predominantly axial. The kinetics of decomposition of 5(6)-hydroxy-6(5)-hydroperoxy-5,6-dihydrothymidine were studied at 22, 37, and 55-degrees-C in ultrapure water. The cis diastereomers of each group were generally found to be more stable than the corresponding trans diastereomers. The enthalpy (DELTAH(double dagger)) and entropy (DELTAS(double dagger)) of decomposition were in the range of 22.9-25.2 kcal mol-1 (DELTAH(double dagger) and -7.4-+3.7 cal mol-1 deg-1 (DELTAS)(double dagger)) for 5-hydroxy-6-hydroperoxy-5,6-dihydrothymidine and in the range 28.5-35.2 kcal mol-1 (DELTAH(double dagger)) and +9.7-+30 cal mol-1 deg-1 (DELTAS(double dagger)) for 5-hydroperoxy-6-hydroxy-5,6-dihydrothymidine. The mechanism of decomposition was studied by analysis of stable and intermediate products: the major decomposition products of the trans and cis diasteromers of 5-hydroxy-6-hydroperoxy-5,6-dihydrothymidine were N-(2-deoxy-beta-D-erythro-pento-furanosyl)-5-hydroxy-5-methylbarbituric acid and N1-(2-deoxy-beta-D-erythro-pentofuranosyl-N3-tartronoylurea in neutral aqueous solutions; in contrast, the trans and cis diastereomers of 5-hydroperoxy-6-hydroxy-5,6-dihydrothymidine were observed to undergo isomerization and ultimately decomposed into the 5R* and 5S* diastereomers of N-(2-deoxy-beta-D-erythro-pentofuranosyl)-5-hydroxy-5-methylhydantoin. On the basis of the above results, the mechanism of decomposition was proposed to involve either dehydration for 5-hydroxy-6-hydroperoxy-5,6-dihydrothymidine or ring-chain tautomerism followed by alpha-cleavage of an intermediate hydroperoxy aldehyde and subsequent ring closure for 5-hydroperoxy-6-hydroxy-5,6-dihydrothymidine.
• Cell culture medium
  申请人：Genetix Limited

  公开号：EP1818392B1

  公开（公告）日：2010-08-25
• CELL CULTURE MEDIUM
  申请人：Bramke Irene

  公开号：US20110104754A1

  公开（公告）日：2011-05-05

  We describe a method of growing an animal cell in a culture medium, in which the culture medium comprises an elevated concentration of a thymidine family member, in which the growth or viability of the animal cell is increased as a result of the elevated concentration of the thymidine family member in the cell culture medium. Preferably, the cell culture medium comprises a semi-solid medium, which is a serum free or chemically defined medium.