(5R)-5-hydroxy-5,6-dihydrothymidine | 78216-58-7

• 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: (5R)-5-hydroxy-5,6-dihydrothymidine
• 英文别名: 5-Hydroxy-thymidine；(5R)-5-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 78216-58-7
• 化学式: C₁₀H₁₆N₂O₆
• 分子量: 260.247
• InChiKey: MRODUHNLAXSPFV-MPXCPUAZSA-N

物化性质

• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲酰腈 、 (5R)-5-hydroxy-5,6-dihydrothymidine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到5'-benzoyl-5,6-dihydro-5-hydroxy-thymidine
  参考文献：
  名称：

  胸苷主要羟基自由基加合物的光化学生成和反应性

  摘要：

  5,6-二氢-5-羟基胸苷-6-基自由基 ( 1 ) 是由羟基自由基加成到嘧啶的 C5 产生的主要反应中间体，通过 2,5-二甲氧基苯硫醚前体 ( 2 ) 的350 nm 光解产生. O 2和硫醇之间的1竞争表明，与其他烷基自由基相比，该自由基与 β-巯基乙醇的反应相对较慢。总的来说，芳基硫化物2应该是 DNA 中胸苷主要羟基自由基加合物的有效前体。

  DOI：

  10.1021/ol301109z
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基咔唑 、 水 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 乙腈 、 叔丁醇 为溶剂， 生成 (5R)-5-hydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Independent generation of the major adduct of hydroxyl radical and thymidine. Examination of intramolecular hydrogen atom transfer in competition with thiol trapping.

  摘要：

  5,6-Dihydro-5-hydroxythymid-6-yl (1) has been generated from 2 via photoinduced electron transfer from N-methylcarbazole. In agreement with prior reports, deuterium incorporation in conjunction with H-2 NMR analysis of 5,6-dihydro-5-hydroxythymidine (3) formed from 1 provides no evidence for intramolecular hydrogen atom abstraction.

  DOI：

  10.1016/s0040-4039(00)60005-9

文献信息

• Radiation-induced binding of 2,2,6,6-tetramethyl-1,4-piperidone-<i>N</i>-oxyl to thymidine in oxygen-free aqueous solutions. Isolation and characterization of the adducts
  作者：Maurice Berger、Jean Cadet、Jacques Ulrich

  DOI：10.1139/v85-002

  日期：1985.1.1

  Steady-state γ-radiolysis of deaerated aqueous solutions of thymidine has been carried out in the presence of 2,2,6,6-tetramethyl-1,4-piperidone-N-oxyl (TAN), a well-known radiosensitizing agent. The eight main radiation-induced TAN addition products to thymidine have been isolated and characterized by 1H and 13C nmr, cd, and fast-atom bombardment mass spectrometry measurements.

  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。
• Sonochemical transformation of thymidine: A mass spectrometric study
  作者：Jisha Chandran、Usha K. Aravind、C.T. Aravindakumar

  DOI：10.1016/j.ultsonch.2015.05.016

  日期：2015.11

  Ultrasound is extensively used in medical field for a number of applications including targeted killing of cancer cells. DNA is one of the most susceptible entities in any kind of free radical induced reactions in living systems. In the present work, the transformation of thymidine (dT) induced by ultrasound (US) was investigated using high resolution mass spectrometry (LC-Q-ToF-MS). dT was subjected

  超声在医学领域已广泛用于许多应用，包括靶向杀死癌细胞。DNA是生命系统中任何种类的自由基诱导的反应中最易感的实体之一。在当前的工作中，使用高分辨率质谱（LC-Q-ToF-MS）研究了超声（US）诱导的胸腺嘧啶核苷（dT）的转化。在充气和氩气饱和条件下，dT在四种不同的频率（200、350、620和1000 kHz）和三种功率密度（10.5、24.5和42 W / mL）下进行声处理。通过LC-Q-ToF-MS检测到总共20种修饰的核苷，包括未完全表征的dT二聚化合物。在这些产物中，仅在氩气气氛中获得了七种，而仅在充气条件下获得了两种。在确定的产品中，有基础改性产品和糖改性产品。产物是通过羟基自由基和氢原子的反应形成的。在充气条件下，反应通过氢过氧化物的形成而进行，而在氩气气氛中歧化和自由基重组占主导。该研究提供了dT的声化学转化途径的完整图片，该途径与超声暴露下的DNA损伤有关。
• Diastereoselective synthesis of hydroxylated dihydrothymidines resulting from oxidative stress
  作者：Mark R. Barvian、Marc M. Greenberg

  DOI：10.1021/jo00074a057

  日期：1993.10
• Site-Specific Incorporation of the Alkaline Labile, Oxidative Stress Product (5R)-5,6-Dihydro-5-hydroxythymidine in an Oligonucleotide
  作者：Tracy J. Matray、Marc M. Greenberg

  DOI：10.1021/ja00094a056

  日期：1994.7
• Reactivity of 5,6-Dihydro-5-hydroxythymid-6-yl Generated via Photoinduced Single Electron Transfer and the Role of Cyclohexa-1,4-diene in the Photodeoxygenation Process
  作者：Mark R. Barvian、Robert M. Barkley、Marc M. Greenberg

  DOI：10.1021/ja00122a021

  日期：1995.5

  The major reactive species formed via reaction of hydroxyl radical and the pyrimidine nucleoside thymidine, 5,6-dihydro-5-hydroxythymid-6-yl (1), is generated photochemically under anaerobic conditions from 6 via photoinduced single electron transfer. Under the conditions in which it is generated, 1 is trapped by hydrogen atom donors to form thymidine C5-hydrate (7), and undergoes oxidation, resulting in the formation of thymidine glycol (8). Isotopic (H-2, O-18) labeling experiments indicate that dehydration of 1 is not competitive with intermolecular hydrogen atom donation by 3,3,6,6-tetradeuteriocyclohexa-1,4-diene. Extrapolation of the known rate constants for hydrogen atom donation by cyclohexa-1,4-diene to alkyl radicals suggests that intramolecular hydrogen atom abstraction and dehydration are <2 s(-1), and are not kinetically competent to be involved in nucleic acid strand scission that arises from 1. Relative quantum yields for disappearance of 6 in the presence and absence of cyclohexa-1,4-diene suggest that the diene reduces the N-methylcarbazole cation radical, preventing back electron transfer. Labeling studies using 3,3,6,6-tetradeuteriocyclohexa-1,4-diene and 1,2,3,4,5,6-hexadeuteriocyclohexa-1,4-diene suggest that the resulting olefin cation radical, or other reactive species derived from the trap, competes with cyclohexa-1,4-diene for 1.