2'-deoxyadenylyl-(3'->5')-2'-deoxycytidine | 23339-46-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 2'-deoxyadenylyl-(3'->5')-2'-deoxycytidine
• 英文别名: d[ApC]；5'-dApdC-3'；2'-deoxy-cytidylyl-(5'->3')-2'-deoxy-adenosine；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl [(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 23339-46-0
• 化学式: C₁₉H₂₅N₈O₉P
• 分子量: 540.429
• InChiKey: QYDPROPQRFNEDI-IDMWBNCISA-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)：
  -3.8
• 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'-deoxyadenylyl-(3'->5')-2'-deoxycytidine 在 bovine intestinal mucosa phosphodiesterase I 、 Tris-Cl buffer 作用下， 反应 1.0h， 生成 2' -脱氧3' -磷酸游离酸 、 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：

  N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 1,1,2,3-四甲基胍 、 syn-2-硝基苯甲醛肟[脱保护剂] 、 双(2-氯苯基)磷酰氯 、 氨 、 水 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 44.49h， 生成 2'-deoxyadenylyl-(3'->5')-2'-deoxycytidine
  参考文献：
  名称：

  Reese, Colin B.; Quanlai, Song, Journal of the Chemical Society. Perkin transactions I, 1999, # 11, p. 1477 - 1486

  摘要：

  DOI：

文献信息

• A New Approach to Oligonucleotide Synthesis in Solution
  作者：Colin B. Reese*、Quanlai. Song

  DOI：10.1080/07328319808004743

  日期：1998.9

  A new approach, based on the use of 3'-H-phosphonate building blocks, is described for the synthesis of oligonucleotides and their phosphorothioate analogues in solution.
• Reese, Colin B.; Quanlai, Song, Journal of the Chemical Society. Perkin transactions I, 1999, # 11, p. 1477 - 1486
  作者：Reese, Colin B.、Quanlai, Song

  DOI：——

  日期：——
• 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.