5'-d(pCpC)-3' | 26467-02-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 5'-d(pCpC)-3'
• 英文别名: d(pC)₂；pdCpC；2'-deoxy-cytidylyl-(5'->3')-2'-deoxy-[5']cytidylic acid；dpC-dpC；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 26467-02-7
• 化学式: C₁₈H₂₆N₆O₁₃P₂
• 分子量: 596.384
• InChiKey: HTZKKVLICDYWHR-PHEULEMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  279
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5'-d(pCpC)-3' 在 2,2'-二硫二吡啶 、 三苯基膦 、 三丁基焦磷酸铵 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.45h， 生成 pppd(CC)
  参考文献：
  名称：

  A facile and effective synthesis of dinucleotide 5′-triphosphates

  摘要：

  We report on the successful synthetic procedure for the conversion of 5 '-monophosphorylated 2 '-deoxydinucleotides into their 5 '-triphosphate derivatives in satisfactory to excellent yields. The activation of the terminal phosphate group was achieved under the Mukaiyama conditions in the presence of a nucleophilic catalyst. The reaction conditions (solvent, counter ions, activation time and reagent excess) were optimized for all dinucleotides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.002
• 作为产物：
  描述：

  4-Methoxy-benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[[(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-phosphonooxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-tetrahydro-furan-3-yl ester 在 吡啶 、 ammonium hydroxide 作用下， 反应 12.0h， 生成 5'-d(pCpC)-3'
  参考文献：
  名称：

  Jankowska, Jadwiga; Stawinski, Jacek, Bulletin of the Polish Academy of Sciences: Chemistry, 1983, vol. 31, # 1-2, p. 17 - 22

  摘要：

  DOI：

文献信息

• Gas Phase Reactions of Trimethylborate with the [M − H]− Ions of Nucleotides and Their Non-Covalent Homo- and Heterodimer Complexes
  作者：Ana K. Vrkic、Richard A. J. O'Hair

  DOI：10.1071/ch02183

  日期：——

  heterodimers. In addition, the collision-induced dissociation (CID) reactions of the [(dXMP)n − H]– (n = 1 or 2) as well as the [dXMP + dYMP – H + (CH3O)3B – 3(CH3OH)]– ions (where nucleotides X, Y = A, C, G, or T) were studied. The latter fragment to form [dXMP – H + BPO4]– and [dXMP – 3H + BPO3]– ions (where X = A, C, G, or T), while [dXMP – H]– ions fragment by neutral base loss. The homo- and heterodimers

  硼酸三甲酯 (TMB) 与核苷酸的去质子化单体、同源和异源二聚体离子（2'-deoxyadenosine-5'-monophosphate [dAMP]、2'-deoxycytidine-5'-monophosphate [dCMP]、2'-deoxyguanosine-5 '-单磷酸盐 [dGMP] 和 2'-脱氧胸苷-5'-单磷酸盐 [dTMP]）在四极离子阱质谱仪中通过添加同时消除一个或两个甲醇分子（单体）、一个或三个甲醇分子（同二聚体） ) 和三个甲醇分子（异二聚体）。反应模式似乎会影响观察到的速率，只有一个甲醇分子的损失对应于最快的速率。单体似乎存在结构-反应性相关性，[dGMP – H]– 离子（采用鸟嘌呤部分的顺式构象）通过仅损失一个甲醇分子与 TMB 反应最快。对于同二聚体和异二聚体，没有观察到这样的结构反应趋势。此外，[(dXMP)n - H]– (n = 1 或 2) 以及
• Jankowska, Jadwiga; Stawinski, Jacek, Bulletin of the Polish Academy of Sciences: Chemistry, 1983, vol. 31, # 1-2, p. 17 - 22
  作者：Jankowska, Jadwiga、Stawinski, Jacek

  DOI：——

  日期：——
• A facile and effective synthesis of dinucleotide 5′-triphosphates
  作者：Tatiana V. Abramova、Svetlana V. Vasileva、Inna Yu. Serpokrylova、Hadar Kless、Vladimir N. Silnikov

  DOI：10.1016/j.bmc.2007.07.002

  日期：2007.10

  We report on the successful synthetic procedure for the conversion of 5 '-monophosphorylated 2 '-deoxydinucleotides into their 5 '-triphosphate derivatives in satisfactory to excellent yields. The activation of the terminal phosphate group was achieved under the Mukaiyama conditions in the presence of a nucleophilic catalyst. The reaction conditions (solvent, counter ions, activation time and reagent excess) were optimized for all dinucleotides. (c) 2007 Elsevier Ltd. All rights reserved.