3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5'-(2-cyanoethyl diisopropylphosphoramidite)

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5'-(2-cyanoethyl diisopropylphosphoramidite)
• 英文别名: [(2R,3S,5R)-2-[[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2-(2-nitrophenyl)propyl carbonate
• 化学式: C₂₉H₄₀N₅O₁₀P
• 分子量: 649.638
• InChiKey: QHMNCYNLPGJEEZ-GPZIPZSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  186
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-(2-硝基苯基)-2-甲基乙基氯甲酸酯 在 吡啶 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 5'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  3‘-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-Fidelity Automated 5‘ → 3‘ Photochemical DNA Synthesis

  摘要：

  The most powerful DNA microarrays would be prepared by photolithography with free 3'-ends that could be processed enzymatically, A photoremovable group that could be removed in quantitative yield would ensure high purity of the synthesized probes. We have developed new pyrimidine building blocks for 5' - 3' DNA synthesis with high cycle yields using the NPPOC (3' nitrophenylpropyloxycarbonyl) protecting group. These phosphoramidites were proved in automated photochemical DNA synthesis on a modified synthesizer.

  DOI：

  10.1021/ol0069150

文献信息

• Synthesis of Photolabile 5′-O-Phosphoramidites for the Photolithographic Production of Microarrays of Inversely Oriented Oligonucleotides
  作者：Markus Beier、Achim Stephan、Jörg D. Hoheisel

  DOI：10.1002/1522-2675(20010711)84:7<2089::aid-hlca2089>3.0.co;2-0

  日期：2001.7.11

  The photolabile 3 ' -O-[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5 ' -phosphoramidites (16-18) were synthesized (see Scheme) for an alternative mode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric building blocks, photolithographic in situ DNA synthesis occurred in 5 ' --> 3 ' direction, in agreement with the orientation of enzymatic synthesis. Synthesis yields were as good as those of conventional reactions. The resulting oligonucleotides are attached to the: surface via their 5 ' -termini, while the 3 ' -hydroxy groups are available as substrates for enzymatic reactions such as primer extension upon hybridization of a DNA template (see Fig. 2). The production of such oligonucleotide chips adds new procedural avenues to the growing number of applications of DNA microarrays.
• US6756492B1
  申请人：——

  公开号：US6756492B1

  公开（公告）日：2004-06-29
• 3‘-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-Fidelity Automated 5‘ → 3‘ Photochemical DNA Synthesis
  作者：Michael C. Pirrung、Laixin Wang、Michael P. Montague-Smith

  DOI：10.1021/ol0069150

  日期：2001.4.1

  The most powerful DNA microarrays would be prepared by photolithography with free 3'-ends that could be processed enzymatically, A photoremovable group that could be removed in quantitative yield would ensure high purity of the synthesized probes. We have developed new pyrimidine building blocks for 5' - 3' DNA synthesis with high cycle yields using the NPPOC (3' nitrophenylpropyloxycarbonyl) protecting group. These phosphoramidites were proved in automated photochemical DNA synthesis on a modified synthesizer.