8-propylthio-2'-deoxyadenosine | 157946-88-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-propylthio-2'-deoxyadenosine
• 英文别名: (2R,3S,5R)-5-(6-amino-8-propylsulfanylpurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 157946-88-8
• 化学式: C₁₃H₁₉N₅O₃S
• 分子量: 325.392
• InChiKey: JVQRBOZPJXECJA-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-propylthio-2'-deoxyadenosine 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-8-propylsulfanylpurin-6-yl]benzamide
  参考文献：
  名称：

  Hydrolysis of oligonucleotides containing 8-substituted purine nucleosides. A new route for preparing abasic oligodeoxynucleotides

  摘要：

  2'-Deoxyadenosine substituted at C-8 by a propylthio group was introduced into oligodeoxyribonucleotides by solid phase synthesis. Oxidation by potassium persulfate (oxone) occurred selectively on the sulfur containing nucleoside causing a weakening of the glycosidic bond. Subsequent hydrolytic treatment led to selective removal of the modified base and generation of an abasic site. This constitutes a novel and convenient route for the chemical synthesis of oligodeoxyribonucleotides containing an abasic site at a preselected position in the sequence.

  DOI：

  10.1016/s0040-4039(00)73301-6
• 作为产物：
  描述：

  2'-脱氧腺苷 、 alkaline earth salt of/the/ methylsulfuric acid 在 硫化氢 、 溴 作用下， 生成 8-propylthio-2'-deoxyadenosine
  参考文献：
  名称：

  Hydrolysis of oligonucleotides containing 8-substituted purine nucleosides. A new route for preparing abasic oligodeoxynucleotides

  摘要：

  2'-Deoxyadenosine substituted at C-8 by a propylthio group was introduced into oligodeoxyribonucleotides by solid phase synthesis. Oxidation by potassium persulfate (oxone) occurred selectively on the sulfur containing nucleoside causing a weakening of the glycosidic bond. Subsequent hydrolytic treatment led to selective removal of the modified base and generation of an abasic site. This constitutes a novel and convenient route for the chemical synthesis of oligodeoxyribonucleotides containing an abasic site at a preselected position in the sequence.

  DOI：

  10.1016/s0040-4039(00)73301-6

文献信息

• Hydrolysis of 2′-deoxypurine nucleosides. The effect of substitution at the C-8 position
  作者：Ali Laayoun、Jean-Luc Décout、Jean Lhomme

  DOI：10.1016/s0040-4039(00)73300-4

  日期：1994.7

  The hydrolytic stability of 2'-deoxypurine nucleosides is decreased by introduction of electron-withdrawing substituents at the C-8 position in the series of compounds 2-8, 10-14. The sulfone group causes a 2.9 x 10(4) rate acceleration for glycosidic bond cleavage in compound 14.
• Hydrolysis of oligonucleotides containing 8-substituted purine nucleosides. A new route for preparing abasic oligodeoxynucleotides
  作者：Ali Laayoun、Jean-Luc Décout、Eric Defrancq、Jean Lhomme

  DOI：10.1016/s0040-4039(00)73301-6

  日期：1994.7

  2'-Deoxyadenosine substituted at C-8 by a propylthio group was introduced into oligodeoxyribonucleotides by solid phase synthesis. Oxidation by potassium persulfate (oxone) occurred selectively on the sulfur containing nucleoside causing a weakening of the glycosidic bond. Subsequent hydrolytic treatment led to selective removal of the modified base and generation of an abasic site. This constitutes a novel and convenient route for the chemical synthesis of oligodeoxyribonucleotides containing an abasic site at a preselected position in the sequence.