8-methyl-N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilylguanosine | 634612-47-8

• 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: 8-methyl-N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilylguanosine
• 英文别名: 8-methyl-N²-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilylguanosine
• CAS: 634612-47-8
• 化学式: C₄₂H₅₃N₅O₈Si
• 分子量: 783.997
• InChiKey: JRHZYDSQVLSZLK-AQOIBLHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  159.05
• 氢给体数：
  3.0
• 氢受体数：
  11.0

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 、 8-methyl-N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilylguanosine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-8-methyl-6-oxo-1H-purin-2-yl]-2-methylpropanamide
  参考文献：
  名称：

  8-Methylguanosine:  A Powerful Z-DNA Stabilizer

  摘要：

  Various modified guanine derivatives were synthesized and introduced into G(4) Of d(CGCGCG)(2) to evaluate their capacity to stabilize Z-form DNA. It was found that the incorporation of 8-methylguanosine (m(8)rG) in oligonucleotides stabilizes the Z form more dramatically than does the incorporation of 8-methyl-2'-deoxyguanosine (m(8)G). This enhancement is ascribed to a reduction in the entropic penalty, which arises from the introduction of hydrophilic groups in solvent-exposed regions. they incorporation of m(8)rG into DNA sequences markedly stabilizes the Z form even in the absence of NaCl. The Z-DNA stabilizer allows oligonucleotides with a wide range of sequences to be converted to the Z form. It could be a powerful tool for examining the molecular basis of many types of Z-form-specific reactions at the molecular level under physiological salt conditions.

  DOI：

  10.1021/ja036233i
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 吡啶 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 8-methyl-N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilylguanosine
  参考文献：
  名称：

  8-Methylguanosine:  A Powerful Z-DNA Stabilizer

  摘要：

  Various modified guanine derivatives were synthesized and introduced into G(4) Of d(CGCGCG)(2) to evaluate their capacity to stabilize Z-form DNA. It was found that the incorporation of 8-methylguanosine (m(8)rG) in oligonucleotides stabilizes the Z form more dramatically than does the incorporation of 8-methyl-2'-deoxyguanosine (m(8)G). This enhancement is ascribed to a reduction in the entropic penalty, which arises from the introduction of hydrophilic groups in solvent-exposed regions. they incorporation of m(8)rG into DNA sequences markedly stabilizes the Z form even in the absence of NaCl. The Z-DNA stabilizer allows oligonucleotides with a wide range of sequences to be converted to the Z form. It could be a powerful tool for examining the molecular basis of many types of Z-form-specific reactions at the molecular level under physiological salt conditions.

  DOI：

  10.1021/ja036233i

文献信息

• EP1604995
  申请人：——

  公开号：——

  公开（公告）日：——