2'-deoxy-O²,O⁶-bis-[2-(4-nitrophenyl)ethyl]xanthosine | 123107-74-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-deoxy-O²,O⁶-bis-[2-(4-nitrophenyl)ethyl]xanthosine
• 英文别名: 2,6-Bis-O-[2-(4-nitrophenyl)ethyl]-2'-deoxyxanthosine；(2R,3S,5R)-5-[2,6-bis[2-(4-nitrophenyl)ethoxy]purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 123107-74-4
• 化学式: C₂₆H₂₆N₆O₉
• 分子量: 566.527
• InChiKey: HEBMQTRBNWXSGT-BHDDXSALSA-N

物化性质

• 沸点：
  861.1±75.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  203
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2'-deoxy-O²,O⁶-bis-[2-(4-nitrophenyl)ethyl]xanthosine 在 N,N-二异丙基乙胺 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 22.25h， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-O²,O⁶-bis-[2-(4-nitrophenyl)ethyl]xanthosine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  使用亚磷酰胺化学合成和表征含有 2'-脱氧黄苷的寡核苷酸

  摘要：

  Oligodeoxynucleotides containing 2'-deoxyxanthosine (X-d) were synthesized in good yield from a O-2,O-6-bis[2-(4-nitrophenyl)ethyl](NPE)-protected phosphoramidite of X-d. Attempts to synthesize a O-6-monoNPE-protected phosphoramidite resulted in formation of a major by-product. The NPE protecting groups were removed by treatment with oximate ion after other protecting groups were removed with aqueous NH,OH solution. The composition of the synthetic oligonucleotides was verified by enzymatic degradation and MALDI-TOF mass spectrometry. The efficacy of this procedure allowed isolation of oligodeoxynucleotides containing multiple X-d residues.

  DOI：

  10.1002/1522-2675(20000705)83:7<1517::aid-hlca1517>3.0.co;2-s
• 作为产物：
  描述：

  2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate 在 氨 、 溶剂黄146 、 silver carbonate 、 sodium nitrite 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 40.0h， 生成 2'-deoxy-O²,O⁶-bis-[2-(4-nitrophenyl)ethyl]xanthosine
  参考文献：
  名称：

  使用亚磷酰胺化学合成和表征含有 2'-脱氧黄苷的寡核苷酸

  摘要：

  Oligodeoxynucleotides containing 2'-deoxyxanthosine (X-d) were synthesized in good yield from a O-2,O-6-bis[2-(4-nitrophenyl)ethyl](NPE)-protected phosphoramidite of X-d. Attempts to synthesize a O-6-monoNPE-protected phosphoramidite resulted in formation of a major by-product. The NPE protecting groups were removed by treatment with oximate ion after other protecting groups were removed with aqueous NH,OH solution. The composition of the synthetic oligonucleotides was verified by enzymatic degradation and MALDI-TOF mass spectrometry. The efficacy of this procedure allowed isolation of oligodeoxynucleotides containing multiple X-d residues.

  DOI：

  10.1002/1522-2675(20000705)83:7<1517::aid-hlca1517>3.0.co;2-s

文献信息

• Redesigned tetrads with altered hydrogen bonding patterns enable programming of quadruplex topologies
  作者：Armin Benz、Jörg S. Hartig

  DOI：10.1039/b805227a

  日期：——

  Guanosine analogs assemble to unusual nucleobase tetrads, restricting possible conformations of four-stranded DNAs.

  鸟苷类似物会聚合成不寻常的核苷酸四联体，从而限制四链DNA的可能构象。
• Synthesis and Characterization of Oligonucleotides Containing 2′-Deoxyxanthosine Using Phosphoramidite Chemistry
  作者：Simona C. Jurczyk、Jennifer Horlacher、Kevin G. Devined、Steven A. Benner、Thomas R. Battersby

  DOI：10.1002/1522-2675(20000705)83:7<1517::aid-hlca1517>3.0.co;2-s

  日期：2000.7.5

  Oligodeoxynucleotides containing 2'-deoxyxanthosine (X-d) were synthesized in good yield from a O-2,O-6-bis[2-(4-nitrophenyl)ethyl](NPE)-protected phosphoramidite of X-d. Attempts to synthesize a O-6-monoNPE-protected phosphoramidite resulted in formation of a major by-product. The NPE protecting groups were removed by treatment with oximate ion after other protecting groups were removed with aqueous NH,OH solution. The composition of the synthetic oligonucleotides was verified by enzymatic degradation and MALDI-TOF mass spectrometry. The efficacy of this procedure allowed isolation of oligodeoxynucleotides containing multiple X-d residues.