2'-deoxy-N⁶-phthaloylcytidine | 199800-43-6

• 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: 2'-deoxy-N⁶-phthaloylcytidine
• 英文别名: 2-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]isoindole-1,3-dione
• CAS: 199800-43-6
• 化学式: C₁₇H₁₅N₃O₆
• 分子量: 357.323
• InChiKey: SZMAFRHUJPNPPY-OUCADQQQSA-N

物化性质

• 沸点：
  628.7±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  121.96
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-N⁶-phthaloylcytidine 在 吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 4 Angstroem MS 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloylcytidine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

  摘要：

  A new alternative strategy of oligonucleotide synthesis was developed by use of thr phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9 - 12). This approach combines the advantages of cheap and easily accessable monomeric building blocks (see 17 - 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<633::aid-hlca633>3.0.co;2-u
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.25h， 生成 2'-deoxy-N⁶-phthaloylcytidine
  参考文献：
  名称：

  Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

  摘要：

  A new alternative strategy of oligonucleotide synthesis was developed by use of thr phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9 - 12). This approach combines the advantages of cheap and easily accessable monomeric building blocks (see 17 - 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<633::aid-hlca633>3.0.co;2-u

文献信息

• Synthesis and Properties of DNA Oligomers Containing 2‘-Deoxynucleoside <i>N</i>-Oxide Derivatives
  作者：Hirosuke Tsunoda、Akihiro Ohkubo、Haruhiko Taguchi、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/jo7021845

  日期：2008.2.1

  reported about the chemical and biochemical behavior of initially formed DNA oligomers containing these N-oxide bases. In this study, we established a convenient method for the solid-phase synthesis of oligodeoxynucleotides incorporating 2‘-deoxycytidine N-oxide (dCO) or 2‘-deoxyadenosine N-oxide (dAO) by using the postsynthetic oxidation of N-protected DNA oligomers except for the target dC or dA site

  长期以来，人们一直认为胞嘧啶和腺嘌呤N-氧化物衍生物是由过氧化物（例如过氧化氢）对DNA的氧化破坏而产生的产物。尽管已经很好地描述了2'-脱氧核苷N-氧化物衍生物的合成和性质，但是关于最初形成的包含这些N-氧化物碱基的DNA低聚物的化学和生物化学行为的报道很少。在这项研究中，我们建立了一种方便的固相合成寡脱氧核苷酸的方法，其中包含2'-脱氧胞苷N-氧化物（dC O）或2'-脱氧腺苷N-氧化物（dA O），使用m- CPBA在MeOH中以高度选择性的方式使用N-保护的DNA低聚物（目标dC或dA位点除外）进行后合成氧化。在该策略中，苯甲酰基，邻苯二甲酰基和（4-异丙基苯氧基）乙酰基被证明可作为碱基保护基团，以避免未修饰位点分别氧化腺嘌呤，胞嘧啶和鸟嘌呤。
• Phthaloyl Strategy—A New Approach Towards Oligodeoxyribonucleotide Synthesis
  作者：Markus Beier、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006240

  日期：1997.7

  A new rapid strategy for machine-aided oligodeoxyribonucleotide synthesis has been established utilizing phthaloyl groups for protection of the heterocyclic amino functions within the phosphoramidite approach. A large number of DNA-sequences has been synthesized. Due to high purity and speed of performance this strategy offers an excellent alternative to the common used acyl approach.