2'-deoxycytidylyl(5'->3')-1'-deoxy-2'-isoadenosine | 265137-12-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 2'-deoxycytidylyl(5'->3')-1'-deoxy-2'-isoadenosine
• 英文别名: 1'-deoxy-2'-isoadenylyl-(3'->5')-2'-deoxycytidine；5'-disoApdC-3'；IsodApdC；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,4R)-4-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 265137-12-0
• 化学式: C₁₉H₂₅N₈O₉P
• 分子量: 540.429
• InChiKey: UHVMTOAALPBXGE-PMTXTEDRSA-N

物化性质

• 沸点：
  901.3±75.0 °C(Predicted)
• 密度：
  2.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  243
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2'-deoxycytidylyl(5'->3')-1'-deoxy-2'-isoadenosine 在 bovine intestinal mucosa phosphodiesterase I 、 Tris-Cl buffer 作用下， 反应 1.0h， 生成 2'-isodeoxy-adenosine 3'-monophosphate 、 2'-脱氧胞嘧啶核苷
  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：

  (2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate 在 吡啶 、 二氯乙酸 、 TPS-TAZ 、 氨 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 2'-deoxycytidylyl(5'->3')-1'-deoxy-2'-isoadenosine
  参考文献：
  名称：

  Recognition and inhibition of HIV integrase by a novel dinucleotide

  摘要：

  The viral enzyme, HIV integrase, is involved in the integration of viral DNA into host cell DNA. In the quest for a small nucleotide system with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered a conceptually novel dinucleotide, pIsodApdC, which is a potent inhibitor of this key viral enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00677-0

文献信息

• Recognition and inhibition of HIV integrase by a novel dinucleotide
  作者：Michael Taktakishvili、Nouri Neamati、Yves Pommier、Vasu Nair

  DOI：10.1016/s0960-894x(99)00677-0

  日期：2000.2

  The viral enzyme, HIV integrase, is involved in the integration of viral DNA into host cell DNA. In the quest for a small nucleotide system with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered a conceptually novel dinucleotide, pIsodApdC, which is a potent inhibitor of this key viral enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Recognition and Inhibition of HIV Integrase by Novel Dinucleotides
  作者：Michael Taktakishvili、Nouri Neamati、Yves Pommier、Suresh Pal、Vasu Nair

  DOI：10.1021/ja992528d

  日期：2000.6.1

  HIV integrase is involved in the integration of viral DNA into chromosomal DNA, a biological process that occurs by a sequence involving HIV DNA splicing and subsequent integration steps. in the quest for small nucleotide systems with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered novel, nuclease-resistant dinucleotides with defined base sequences that are inhibitors of this key viral enzyme. Synthetic methodologies utilized for the syntheses of the novel dinucleotides include an excellent new phosphorylating agent.
• 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.