8-methyl-N²-isobutyrylguanosine | 634612-45-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-methyl-N²-isobutyrylguanosine
• 英文别名: N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-methyl-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 634612-45-6
• 化学式: C₁₅H₂₁N₅O₆
• 分子量: 367.362
• InChiKey: BKHGXASIPROYHL-AKAIJSEGSA-N

物化性质

• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-methyl-N²-isobutyrylguanosine 在 咪唑 、 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 40.0h， 生成 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：

  N2-异丁酰基鸟苷一水合物 、 叔丁基过氧化氢 在 硫酸 、 iron(II) sulfate 作用下， 反应 2.0h， 以59%的产率得到8-methyl-N²-isobutyrylguanosine
  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：——