9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N²-(N,N-(dimethylamino)methylene)guanine | 783322-72-5

• 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: 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N²-(N,N-(dimethylamino)methylene)guanine
• 英文别名: N'-[9-[(1R,3R,4R,5R)-3-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-2,6-dioxabicyclo[3.2.0]heptan-1-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 783322-72-5
• 化学式: C₃₅H₃₆N₆O₇
• 分子量: 652.707
• InChiKey: POZKAPWAIPQEIK-WIFIACMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N²-(N,N-(dimethylamino)methylene)guanine 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到2-(4-乙氧基苯基)-3-[4-(甲基磺酰基)苯基]吡唑并[1,5-b]哒嗪
  参考文献：
  名称：

  Synthesis, Physicochemical and Biochemical Studies of 1‘,2‘-Oxetane Constrained Adenosine and Guanosine Modified Oligonucleotides, and Their Comparison with Those of the Corresponding Cytidine and Thymidine Analogues

  摘要：

  We have earlier reported the synthesis and antisense properties of the conformationally constrained oxetane-C and -T containing oligonucleotides, which have shown effective down-regulation of the proto-oncogene c-myb mRNA in the K562 human leukemia cells. Here we report on the straightforward syntheses of the oxetane-A and oxetane-G nucleosides as well as their incorporations into antisense oligonucleotides (AONs), and compare their structural and antisense properties with those of the T and C modified AONs (including the thermostability and RNase H recruitment capability of the AON/RNA hybrid duplex by Michaelis-Menten kinetic analyses, their resistance in the human serum, as well as in the presence of exo and endonucleases).

  DOI：

  10.1021/ja048417i
• 作为产物：
  描述：

  N,N-二苯基-氨基甲酸 2-(乙酰氨基)-9H-嘌呤-6-基酯 在 吡啶 、 N,O-双三甲硅基乙酰胺 、 四丁基氟化铵 、 氨 、 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 56.57h， 生成 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N²-(N,N-(dimethylamino)methylene)guanine
  参考文献：
  名称：

  Synthesis, Physicochemical and Biochemical Studies of 1‘,2‘-Oxetane Constrained Adenosine and Guanosine Modified Oligonucleotides, and Their Comparison with Those of the Corresponding Cytidine and Thymidine Analogues

  摘要：

  We have earlier reported the synthesis and antisense properties of the conformationally constrained oxetane-C and -T containing oligonucleotides, which have shown effective down-regulation of the proto-oncogene c-myb mRNA in the K562 human leukemia cells. Here we report on the straightforward syntheses of the oxetane-A and oxetane-G nucleosides as well as their incorporations into antisense oligonucleotides (AONs), and compare their structural and antisense properties with those of the T and C modified AONs (including the thermostability and RNase H recruitment capability of the AON/RNA hybrid duplex by Michaelis-Menten kinetic analyses, their resistance in the human serum, as well as in the presence of exo and endonucleases).

  DOI：

  10.1021/ja048417i

文献信息

• Synthesis, Physicochemical and Biochemical Studies of 1‘,2‘-Oxetane Constrained Adenosine and Guanosine Modified Oligonucleotides, and Their Comparison with Those of the Corresponding Cytidine and Thymidine Analogues
  作者：Pushpangadan I. Pradeepkumar、Pradeep Cheruku、Oleksandr Plashkevych、Parag Acharya、Suresh Gohil、Jyoti Chattopadhyaya

  DOI：10.1021/ja048417i

  日期：2004.9.1

  We have earlier reported the synthesis and antisense properties of the conformationally constrained oxetane-C and -T containing oligonucleotides, which have shown effective down-regulation of the proto-oncogene c-myb mRNA in the K562 human leukemia cells. Here we report on the straightforward syntheses of the oxetane-A and oxetane-G nucleosides as well as their incorporations into antisense oligonucleotides (AONs), and compare their structural and antisense properties with those of the T and C modified AONs (including the thermostability and RNase H recruitment capability of the AON/RNA hybrid duplex by Michaelis-Menten kinetic analyses, their resistance in the human serum, as well as in the presence of exo and endonucleases).