(6-(2-(6-(4'-methyl-2,2'-bipyridin-4-yl)hexanamido)ethylamino)-9H-purin-9-yl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyriboside | 1013022-68-8

• 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: (6-(2-(6-(4'-methyl-2,2'-bipyridin-4-yl)hexanamido)ethylamino)-9H-purin-9-yl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyriboside
• CAS: 1013022-68-8
• 化学式: C₅₀H₅₄N₈O₆
• 分子量: 863.029
• InChiKey: BKWUANFALVBQOJ-UFCNIINJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  167.66
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (6-(2-(6-(4'-methyl-2,2'-bipyridin-4-yl)hexanamido)ethylamino)-9H-purin-9-yl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyriboside 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到5-O-(4,4'-dimethoxytrityl)-6-N-[9-(4'-methyl-2,2'-bipyridin-4-yl)3-oxa-2-azanonyl]-2'-deoxyadenine 3'-(2-cyanoethyl N,N-diispropylphophosphoramidite)
  参考文献：
  名称：

  An Osmium−DNA Interstrand Complex:  Application to Facile DNA Methylation Analysis

  摘要：

  Nucleic acids often acquire new functions by forming a variety of complexes with metal ions. Osmium, in an oxidized state, also reacts with C5-methylated pyrimidines. However, control of the sequence specificity of osmium complexation with DNA is still immature, and the value of the resulting complexes is unknown. We have designed a bipyridine-attached adenine derivative for sequence-specific osmium complexation. Sequence-specific osmium complexation was achieved by hybridization of a short DNA molecule containing this functional nucleotide to a target DNA sequence and resulted in the formation of a cross-linked structure. The interstrand cross-link clearly distinguished methylated cytosines from unmethylated cytosines and was used to quantify the degree of methylation at a specific cytosine in the genome.

  DOI：

  10.1021/ja076140r
• 作为产物：
  描述：

  N-(2-aminoethyl)-6-(4'-methyl-[2,2'-bipyridin]-4-yl)hexanamide 、 6-chloro-9-(2-deoxy-5-O-dimethoxytrityl-β-D-erythro-pentofuranosyl)purine 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以95%的产率得到(6-(2-(6-(4'-methyl-2,2'-bipyridin-4-yl)hexanamido)ethylamino)-9H-purin-9-yl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyriboside
  参考文献：
  名称：

  An Osmium−DNA Interstrand Complex:  Application to Facile DNA Methylation Analysis

  摘要：

  Nucleic acids often acquire new functions by forming a variety of complexes with metal ions. Osmium, in an oxidized state, also reacts with C5-methylated pyrimidines. However, control of the sequence specificity of osmium complexation with DNA is still immature, and the value of the resulting complexes is unknown. We have designed a bipyridine-attached adenine derivative for sequence-specific osmium complexation. Sequence-specific osmium complexation was achieved by hybridization of a short DNA molecule containing this functional nucleotide to a target DNA sequence and resulted in the formation of a cross-linked structure. The interstrand cross-link clearly distinguished methylated cytosines from unmethylated cytosines and was used to quantify the degree of methylation at a specific cytosine in the genome.

  DOI：

  10.1021/ja076140r