7-(2-deoxy-β-D-erythro-pentofuranosyl)-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione | 1290537-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-(2-deoxy-β-D-erythro-pentofuranosyl)-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione
• CAS: 1290537-74-4
• 化学式: C₁₉H₂₀N₄O₅S
• 分子量: 416.458
• InChiKey: XOCCRYWTUXSWDG-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  121.63
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  7-(2-deoxy-β-D-erythro-pentofuranosyl)-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione 在 吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 4-[(2-cyanoethyl)thio]-7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-2-phenoxyacetamido-7H-pyrrolo-[2,3-d]pyrimidine 3'-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]
  参考文献：
  名称：

  DNA Gold Nanoparticle Conjugates Incorporating Thiooxonucleosides: 7-Deaza-6-thio-2′-deoxyguanosine as Gold Surface Anchor

  摘要：

  A new protocol for the covalent attachment of oligonucleotides to gold nanoparticles was developed. Base-modified nucleosides with thiooxo groups were acting as molecular surface anchor. Compared to already existing conjugation protocols, the new linker strategy simplifies the synthesis of DNA gold nanoparticle conjugates. The phosphoramidite of 7-deaza-6-thio-2'-deoxyguanosine (6) was used in solid-phase synthesis. Incorporation of the sulfur-containing nucleosides can be performed at any position of an oligonucleotide; even multiple incorporations are feasible, which will increase the binding stability of the corresponding oligonucleotides to the gold nanoparticles. Oligonucleotide strands immobilized at the end of a chain were easily accessible during hybridization leading to DNA gold nanoparticle network formation. On the contrary, oligonucleotides immobilized via a central position could not form a DNA-AuNP network. Melting studies of the DNA gold nanoparticle assemblies revealed sharp melting profiles with a very narrow melting transition.

  DOI：

  10.1021/bc200069j
• 作为产物：
  描述：

  2-Amino-7-<2-desoxy-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-thion 、 苯氧乙酰氯 在 吡啶 、 三甲基氯硅烷 作用下， 反应 5.0h， 以81%的产率得到7-(2-deoxy-β-D-erythro-pentofuranosyl)-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-thione
  参考文献：
  名称：

  DNA Gold Nanoparticle Conjugates Incorporating Thiooxonucleosides: 7-Deaza-6-thio-2′-deoxyguanosine as Gold Surface Anchor

  摘要：

  A new protocol for the covalent attachment of oligonucleotides to gold nanoparticles was developed. Base-modified nucleosides with thiooxo groups were acting as molecular surface anchor. Compared to already existing conjugation protocols, the new linker strategy simplifies the synthesis of DNA gold nanoparticle conjugates. The phosphoramidite of 7-deaza-6-thio-2'-deoxyguanosine (6) was used in solid-phase synthesis. Incorporation of the sulfur-containing nucleosides can be performed at any position of an oligonucleotide; even multiple incorporations are feasible, which will increase the binding stability of the corresponding oligonucleotides to the gold nanoparticles. Oligonucleotide strands immobilized at the end of a chain were easily accessible during hybridization leading to DNA gold nanoparticle network formation. On the contrary, oligonucleotides immobilized via a central position could not form a DNA-AuNP network. Melting studies of the DNA gold nanoparticle assemblies revealed sharp melting profiles with a very narrow melting transition.

  DOI：

  10.1021/bc200069j