2-[N-(9-fluorenylmethyloxycarbonyl)-aminooxy]-N-{2-hydroxy-3-(4,4'-dimethoxytrityloxy)-propyl}acetamide | 1187430-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-[N-(9-fluorenylmethyloxycarbonyl)-aminooxy]-N-{2-hydroxy-3-(4,4'-dimethoxytrityloxy)-propyl}acetamide
• CAS: 1187430-31-4
• 化学式: C₄₁H₄₀N₂O₈
• 分子量: 688.777
• InChiKey: DGRJQFKVXGTEAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  51.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124.58
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 2-[N-(9-fluorenylmethyloxycarbonyl)-aminooxy]-N-{2-hydroxy-3-(4,4'-dimethoxytrityloxy)-propyl}acetamide 在 4-二甲氨基吡啶 、 三乙胺 、 水 、 柠檬酸 作用下， 以 1,2-二氯乙烷 、 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到10-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-1-(9H-fluoren-9-yl)-3,7,12-trioxo-2,5,11-trioxa-4,8-diazapentadecan-15-oic acid
  参考文献：
  名称：

  Polymer supported synthesis of aminooxyalkylated oligonucleotides, and some applications in the fabrication of microarrays

  摘要：

  A new protocol has been described for solid phase preparation of 3'- and 5'-aminooxylalkylated oligonucleotides using commercially available reagents. This involves attachment of linker 4 either with an LCAA-CPG support via succinoylation followed by synthesis (3'-aminooxyalkylated oligomers) or formation of its phosphoramidite 6 followed by coupling with desired oligomer (for generating 5'-aminooxyalkylated oligomers). Both the routes produced modified oligonucleotides in sufficiently high yields and purity (on HPLC) via conventional oligonucleotide synthesis on an automated synthesizer and deprotection step using aqueous ammonia (16 h, 60 degrees C). Aminooxyalkylated oligonucleotides were used to construct microarrays on glass surface (biochips). The performance of the biochips was evaluated by immobilizing modified oligonucleotides on epoxylated glass microslides under different sets of conditions with respect to pH, temperature and time. Further, the constructed microarrays were successfully used for detection of nucleotide mismatches and bacterial typhoid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.038
• 作为产物：
  描述：

  2-(N-(9-fluorenylmethyloxycarbonyl)aminooxy)-N-(2,3-dihydroxypropyl)acetamide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以85%的产率得到2-[N-(9-fluorenylmethyloxycarbonyl)-aminooxy]-N-{2-hydroxy-3-(4,4'-dimethoxytrityloxy)-propyl}acetamide
  参考文献：
  名称：

  Polymer supported synthesis of aminooxyalkylated oligonucleotides, and some applications in the fabrication of microarrays

  摘要：

  A new protocol has been described for solid phase preparation of 3'- and 5'-aminooxylalkylated oligonucleotides using commercially available reagents. This involves attachment of linker 4 either with an LCAA-CPG support via succinoylation followed by synthesis (3'-aminooxyalkylated oligomers) or formation of its phosphoramidite 6 followed by coupling with desired oligomer (for generating 5'-aminooxyalkylated oligomers). Both the routes produced modified oligonucleotides in sufficiently high yields and purity (on HPLC) via conventional oligonucleotide synthesis on an automated synthesizer and deprotection step using aqueous ammonia (16 h, 60 degrees C). Aminooxyalkylated oligonucleotides were used to construct microarrays on glass surface (biochips). The performance of the biochips was evaluated by immobilizing modified oligonucleotides on epoxylated glass microslides under different sets of conditions with respect to pH, temperature and time. Further, the constructed microarrays were successfully used for detection of nucleotide mismatches and bacterial typhoid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.038