dCpdU | 356518-65-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: dCpdU
• 英文别名: 2'-deoxycytidylyl-(3'->5')-1'-deoxy-2'-isouridine；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,4R)-4-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 356518-65-5
• 化学式: C₁₈H₂₄N₅O₁₁P
• 分子量: 517.389
• InChiKey: FJUMBVWTRMLDMA-LWHUEDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  223
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dCpdU 在 bovine intestinal mucosa phosphodiesterase I 、 Tris-Cl buffer 作用下， 反应 1.0h， 生成 2ˊ-脱氧胞苷-3ˊ-一磷酸 、 1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol
  参考文献：
  名称：

  Resistance towards exonucleases of dinucleotides with stereochemically altered internucleotide phosphate bonds

  摘要：

  Kinetic constants for the hydrolytic susceptibility of the internucleotide phosphate bond in normal dinucleotides [e.g., 2'-deoxycytidylyl-(3' > 5')-2'-deoxyuridine (dCpdU) and 2'-deoxyadenylyl-(3'--> 5')-2-deoxycytidine (dApdC)] and isomeric dinucleotides [e.g., 2-deoxycytidylyl-(3' --> 5')-1'-deoxy-2-isouridine (dCpisodU) and 1'-deoxy-2'-isoadenylyl-(3' --> 5')-2-deoxycytidine (isodApdC)], toward 5'- and 3'-exonucleases, phosphodiesterase I (PDE I) and phosphodiesterase II (PDE II) were experimentally determined and remarkable differences emerged. The study is of importance in the discovery of nuclease-stable inhibitors of HIV integrase, but may also have ramifications in the area of anti-sense oligonucleotides of therapeutic interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.034
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-2-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-D-arabinitol 在 吡啶 、 二氯乙酸 、 ammonium hydroxide 、 TPS-TAZ 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 dCpdU
  参考文献：
  名称：

  Discovery of a nuclease-resistant, non-natural dinucleotide that inhibits HIV-1 integrase

  摘要：

  Integration of HIV viral DNA into human chromosomal DNA catalyzed by HIV integrase is essential for the replication of HIV. Discovery of novel inhibitors of HIV integrase is of considerable significance in approaches to the development of therapeutic agents against AIDS. We have synthesized a new dinucleotide 1 with an internucleotide phosphate bond that is unusually resistant to exonucleases. This compound exhibits potent anti-HIV-1 integrase activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00231-1

文献信息

• Resistance towards exonucleases of dinucleotides with stereochemically altered internucleotide phosphate bonds
  作者：Vasu Nair、Suresh Pal

  DOI：10.1016/j.bmcl.2003.07.034

  日期：2004.1

  Kinetic constants for the hydrolytic susceptibility of the internucleotide phosphate bond in normal dinucleotides [e.g., 2'-deoxycytidylyl-(3' > 5')-2'-deoxyuridine (dCpdU) and 2'-deoxyadenylyl-(3'--> 5')-2-deoxycytidine (dApdC)] and isomeric dinucleotides [e.g., 2-deoxycytidylyl-(3' --> 5')-1'-deoxy-2-isouridine (dCpisodU) and 1'-deoxy-2'-isoadenylyl-(3' --> 5')-2-deoxycytidine (isodApdC)], toward 5'- and 3'-exonucleases, phosphodiesterase I (PDE I) and phosphodiesterase II (PDE II) were experimentally determined and remarkable differences emerged. The study is of importance in the discovery of nuclease-stable inhibitors of HIV integrase, but may also have ramifications in the area of anti-sense oligonucleotides of therapeutic interest. (C) 2003 Elsevier Ltd. All rights reserved.
• Discovery of a nuclease-resistant, non-natural dinucleotide that inhibits HIV-1 integrase
  作者：Michael Taktakishvili、Nouri Neamati、Yves Pommier、Vasu Nair

  DOI：10.1016/s0960-894x(01)00231-1

  日期：2001.6

  Integration of HIV viral DNA into human chromosomal DNA catalyzed by HIV integrase is essential for the replication of HIV. Discovery of novel inhibitors of HIV integrase is of considerable significance in approaches to the development of therapeutic agents against AIDS. We have synthesized a new dinucleotide 1 with an internucleotide phosphate bond that is unusually resistant to exonucleases. This compound exhibits potent anti-HIV-1 integrase activity. (C) 2001 Elsevier Science Ltd. All rights reserved.