胞苷-D2氘代内标 | 40632-25-5

• 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: 胞苷-D2氘代内标
• 英文名称: 5,6-dideuteriocytidine
• 英文别名: 5,6-Dideutero-cytidin；5-D-6-D-Cytidin；Cytidine-d2；5,6-dideuterio-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iminopyrimidin-2-one
• CAS: 40632-25-5
• 化学式: C₉H₁₃N₃O₅
• 分子量: 245.203
• InChiKey: UHDGCWIWMRVCDJ-SXFMXZDVSA-N

物化性质

• 溶解度：
  DMF：可溶，DMSO：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胞苷 在 palladium on activated charcoal 氢气 、 重水 作用下， 反应 48.0h， 以100%的产率得到胞苷-D2氘代内标
  参考文献：
  名称：

  钯催化碱基选择性 HD 交换反应中的核苷在氧化氘中

  摘要：

  我们开发了一种高效且广泛的氘掺入方法，使用异质 Pd/CD 2 OH 2 系统进入核苷的碱基部分。此处介绍的结果提供了一种在 D 2 O 介质中无氘气、完全催化和合成后的氘标记方法。

  DOI：

  10.1055/s-2005-868489

文献信息

• Site of Protonation of One-Electron-Reduced Cytosine and Its Derivatives in Aqueous Methanol Glasses
  作者：Paul M. Cullis、Mark E. Malone、Ian D. Podmore、Martyn C. R. Symons

  DOI：10.1021/j100022a051

  日期：1995.6

  Electron paramagnetic resonance spectra of one-electron-reduced cytosine, cytidine, 2'-deoxycytidine, 5'-dCMP, and 3'-dCMP produced by Co-60 gamma-irradiation in aqueous lithium chloride glasses (LiCl/H2O) and aqueous methanol glasses (MeOH/H2O) at 77 K exhibited a triplet which has been interpreted in terms of the radical anion protonating on the exocyclic amino group of the base C(N4+H)(.) (II), The exchangeable nature of the extra proton coupling is demonstrated by the collapse of the triplet into a doublet in LiCl/D2O and CD3OD/D2O glasses. The EPR spectrum of cytidine-5,6-d(2) in either LiCl glasses or aqueous methanol led to a doublet in each case, consistent with the loss of the coupling to the hydrogen on C6, with the remaining coupling due to the protonation on the exocyclic amino group. Comparable experiments in LiCl/D2O or CD3OD/D2O glasses led directly to a singlet. The results in aqueous methanol glasses parallel closely those in aqueous LiCl glasses and provide clear evidence for protonation on the exocyclic amino group even in the absence of metal ion coordination to N3. Hence, N4 protonation of the cytosine radical anion is not a result of metal ion coordination to N3 as has been suggested by others. We suggest that N4 protonation is kinetically controlled, possibly brought about by solvation effects, whereas the N3 protonation would occur under thermodynamic control.
• Esaki, Hiroyoshi; Aoki, Fumiyo; Maegawa, Tomohiro, Heterocycles, 2005, vol. 66, # 1, p. 361 - 369
  作者：Esaki, Hiroyoshi、Aoki, Fumiyo、Maegawa, Tomohiro、Hirota, Kosaku、Sajiki, Hironao

  DOI：——

  日期：——