N-isobutyryl-5'-O-dimethoxytrityl-8-(2-(trimethylsilyl)ethyl)thio-2'-deoxyguanosine | 794574-98-4

• 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: N-isobutyryl-5'-O-dimethoxytrityl-8-(2-(trimethylsilyl)ethyl)thio-2'-deoxyguanosine
• 英文别名: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-6-oxo-8-(2-trimethylsilylethylsulfanyl)-1H-purin-2-yl]-2-methylpropanamide
• CAS: 794574-98-4
• 化学式: C₄₀H₄₉N₅O₇SSi
• 分子量: 772.01
• InChiKey: DYSNVLLMCKONBX-WIHCDAFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 N-isobutyryl-5'-O-dimethoxytrityl-8-(2-(trimethylsilyl)ethyl)thio-2'-deoxyguanosine 在 N-甲基咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以62%的产率得到2-N-isobutyryl-5'-O-dimethoxytrityl-8-(2-(trimethylsilyl)ethyl)thio-2'-deoxyguanosin-3'-yl β-cyanoethyl-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Oligonucleotide Incorporation of 8-Thio-2‘-deoxyguanosine

  摘要：

  (GRAPHICS)8-Thio-2'-deoxyguanosine (SdG) is a useful analogue of the abundant promutagen 8-oxo-2'-deoxyguanosine (OdG). Its synthesis and DNA incorporation using standard phosphoramidite chemistry is reported. To prevent oxidation during DNA synthesis, the sulfur was protected as a 2-(trimethylsilyl)ethyl sulfide. Subsequent treatment with TBAF yielded the desired 8-thiocarbonyl functionality. Melting studies with SdG revealed almost equal stabilities of SdG:dC and SdG:dA base pairs, lending insight into the base-pairing preferences of OdG.

  DOI：

  10.1021/ol0484097
• 作为产物：
  描述：

  2-(三甲基硅烷)乙硫醇 在 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.5h， 生成 N-isobutyryl-5'-O-dimethoxytrityl-8-(2-(trimethylsilyl)ethyl)thio-2'-deoxyguanosine
  参考文献：
  名称：

  Oligonucleotide Incorporation of 8-Thio-2‘-deoxyguanosine

  摘要：

  (GRAPHICS)8-Thio-2'-deoxyguanosine (SdG) is a useful analogue of the abundant promutagen 8-oxo-2'-deoxyguanosine (OdG). Its synthesis and DNA incorporation using standard phosphoramidite chemistry is reported. To prevent oxidation during DNA synthesis, the sulfur was protected as a 2-(trimethylsilyl)ethyl sulfide. Subsequent treatment with TBAF yielded the desired 8-thiocarbonyl functionality. Melting studies with SdG revealed almost equal stabilities of SdG:dC and SdG:dA base pairs, lending insight into the base-pairing preferences of OdG.

  DOI：

  10.1021/ol0484097

文献信息

• Oligonucleotide Incorporation of 8-Thio-2‘-deoxyguanosine
  作者：Michelle L. Hamm、Rushina Cholera、Courtney L. Hoey、Timothy J. Gill

  DOI：10.1021/ol0484097

  日期：2004.10.1

  (GRAPHICS)8-Thio-2'-deoxyguanosine (SdG) is a useful analogue of the abundant promutagen 8-oxo-2'-deoxyguanosine (OdG). Its synthesis and DNA incorporation using standard phosphoramidite chemistry is reported. To prevent oxidation during DNA synthesis, the sulfur was protected as a 2-(trimethylsilyl)ethyl sulfide. Subsequent treatment with TBAF yielded the desired 8-thiocarbonyl functionality. Melting studies with SdG revealed almost equal stabilities of SdG:dC and SdG:dA base pairs, lending insight into the base-pairing preferences of OdG.