5-(2-phenylethyl)-2'-deoxyuridine | 73847-52-6

• 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: 5-(2-phenylethyl)-2'-deoxyuridine
• 英文别名: 5-Phenethyl-2'-deoxyuridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-phenylethyl)pyrimidine-2,4-dione
• CAS: 73847-52-6
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: VUYCCQZVUDLBHZ-RRFJBIMHSA-N

物化性质

• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-脱氧尿苷 在 palladium on activated charcoal lithium tetrachloropalladate 、 mercury(II) diacetate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 41.0h， 生成 5-(2-phenylethyl)-2'-deoxyuridine
  参考文献：
  名称：

  Palladium-catalyzed coupling reactions of uracil nucleosides and nucleotides

  摘要：

  DOI：

  10.1021/ja00526a044

文献信息

• Parahydrogen‐Induced Polarization of a Labeled, Cancer‐Targeting DNA Aptamer
  作者：Kai-Oliver Brenske、Meike Emondts、Sven Thore Hörnig、Sinan Panitz、Maria Isabell Pieper、Aron Ligori、Alexander Schacht、Johanna Henkel、Jürgen Klankermayer、Andreas Herrmann

  DOI：10.1002/anie.202300531

  日期：——

  We present the unprecedented hyperpolarization of the cancer-targeting aptamer AS1411 via parahydrogen. For that, we screened for suitable parahydrogen-induced polarization (PHIP) labels, performed solid phase synthesis to incorporate the label into AS1411 and adapted the polarity of DNA via PEGylation to enable efficient, selective hydrogenation in organic solvents without affecting canonical nucleotides

  我们通过对氢展示了癌症靶向适体 AS1411 前所未有的超极化。为此，我们筛选了合适的对位氢诱导极化 (PHIP) 标记，进行固相合成以将标记整合到 AS1411 中，并通过聚乙二醇化调整 DNA 的极性，以在不影响规范核苷酸的情况下在有机溶剂中实现高效、选择性氢化。
• Independent Generation and Reactivity of 2‘-Deoxy-5-methyleneuridin-5-yl, a Significant Reactive Intermediate Produced from Thymidine as a Result of Oxidative Stress
  作者：Aaron S. Anderson、Jae-Taeg Hwang、Marc M. Greenberg

  DOI：10.1021/jo000271s

  日期：2000.7.1

  2'-Deoxy-5-methyleneuridin-5-yl (1) is produced in a variety of DNA damage processes and is believed to result in the formation of lesions that are mutagenic and refractory to enzymatic repair. 2'-Deoxy-5-methyleneuridin-5-yl (1) was independently generated under anaerobic conditions via Norrish Type I photocleavage during Pyrex filtered photolysis of the benzyl ketone 7. The radical (1) exhibits behavior consistent with that of a resonance-stabilized radical. The KIE for hydrogen atom transfer from t-BuSH was found to be 7.3 +/- 1.7. Competition studies between radical recombination and hydrogen atom donors (2,5-dimethyltetrahydrofuran, k(Trap) = 46.1 +/- 15.4 M-1 s(-1); propan-2-ol, k(Trap) = 13.6 +/- 3.5 M-1 s(-1)) chosen to mimic the carbohydrate components of 2'-deoxyribonucleotides suggest that 2'-deoxy-5-methyleneuridin-5-yl (1) may be able to transfer damage from the nucleobase to the deoxyribose of an adjacent nucleotide in DNA under hypoxic conditions.
• JPH0717869A
  申请人：——

  公开号：JPH0717869A

  公开（公告）日：1995-01-20
• Palladium-catalyzed coupling reactions of uracil nucleosides and nucleotides
  作者：Christopher F. Bigge、Panos Kalaritis、Joanne R. Deck、Mathias P. Mertes

  DOI：10.1021/ja00526a044

  日期：1980.3