4-[(2-cyanoethyl)thio]-7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidine | 1290537-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-[(2-cyanoethyl)thio]-7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: N-[7-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-4-(2-cyanoethylsulfanyl)pyrrolo[2,3-d]pyrimidin-2-yl]-2-phenoxyacetamide
• CAS: 1290537-76-6
• 化学式: C₄₃H₄₁N₅O₇S
• 分子量: 771.894
• InChiKey: UBMCIZVTEGMWHU-OPWUGURCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-[(2-cyanoethyl)thio]-7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-2-phenoxyacetamido-7H-pyrrolo[2,3-d]pyrimidine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以61%的产率得到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 在 吡啶 、 三甲基氯硅烷 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 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
  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

文献信息

• A CONJUGATE BETWEEN A THIOPHILIC SOLID PHASE AND AN OLIGONUCLEOTIDE COMPRISING A THIOOXONUCLEOTIDE
  申请人：Roche Diagnostics GmbH

  公开号：EP2630255B1

  公开（公告）日：2014-09-10
• DNA Gold Nanoparticle Conjugates Incorporating Thiooxonucleosides: 7-Deaza-6-thio-2′-deoxyguanosine as Gold Surface Anchor
  作者：Frank Seela、Ping Ding、Simone Budow

  DOI：10.1021/bc200069j

  日期：2011.4.20

  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.