Acetic acid (2R,3S)-2-acetoxymethyl-5-(3-benzyloxy-2-methyl-4-oxo-4H-pyridin-1-yl)-tetrahydro-furan-3-yl ester | 500361-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Acetic acid (2R,3S)-2-acetoxymethyl-5-(3-benzyloxy-2-methyl-4-oxo-4H-pyridin-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 500361-26-2
• 化学式: C₂₂H₂₅NO₇
• 分子量: 415.443
• InChiKey: NURXGBTYFGIEIH-MCOCGALXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  93.06
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S)-2-acetoxymethyl-5-(3-benzyloxy-2-methyl-4-oxo-4H-pyridin-1-yl)-tetrahydro-furan-3-yl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 22.5h， 生成
  参考文献：
  名称：

  Efficient Incorporation of a Copper Hydroxypyridone Base Pair in DNA

  摘要：

  Recently, we reported the first artificial nucleoside for alternative DNA base pairing through metal complexation (J. Org. Chem. 1999, 64, 5002-5003). In this regard, we report here the synthesis of a hydroxypyridone-bearing nucleoside and the incorporation of a neutral Cu2+-mediated base pair of hydroxypyridone nucleobases (H-Cu-H) in a DNA duplex. When the hydroxypyridone bases are incorporated into the middle of a 15 nucleotide duplex, the duplex displays high thermal stabilization in the presence of equimolar Cu2+ ions in comparison with a duplex containing an A-T pair in place of the H-H pair. Monitoring temperature dependence of UV-absorption changes verified that a Cu2+-mediated base pair is stoichiometrically formed inside the duplex and dissociates upon thermal denaturation at elevated temperature. In addition, EPR and CD studies suggested that the radical site of a Cu2+ center is formed within the right-handed double-strand structure of the oligonucleotide. The present strategy could be developed for controlled and periodic spacing of neutral metallobase pairs along the helix axis of DNA.

  DOI：

  10.1021/ja027175o
• 作为产物：
  描述：

  1,3,5-tri-O-acetyl-2-deoxyribose 、 3-苄氧基-2-甲基-4(1H)-吡啶酮 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 26.0h， 以70%的产率得到Acetic acid (2R,3S)-2-acetoxymethyl-5-(3-benzyloxy-2-methyl-4-oxo-4H-pyridin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Efficient Incorporation of a Copper Hydroxypyridone Base Pair in DNA

  摘要：

  Recently, we reported the first artificial nucleoside for alternative DNA base pairing through metal complexation (J. Org. Chem. 1999, 64, 5002-5003). In this regard, we report here the synthesis of a hydroxypyridone-bearing nucleoside and the incorporation of a neutral Cu2+-mediated base pair of hydroxypyridone nucleobases (H-Cu-H) in a DNA duplex. When the hydroxypyridone bases are incorporated into the middle of a 15 nucleotide duplex, the duplex displays high thermal stabilization in the presence of equimolar Cu2+ ions in comparison with a duplex containing an A-T pair in place of the H-H pair. Monitoring temperature dependence of UV-absorption changes verified that a Cu2+-mediated base pair is stoichiometrically formed inside the duplex and dissociates upon thermal denaturation at elevated temperature. In addition, EPR and CD studies suggested that the radical site of a Cu2+ center is formed within the right-handed double-strand structure of the oligonucleotide. The present strategy could be developed for controlled and periodic spacing of neutral metallobase pairs along the helix axis of DNA.

  DOI：

  10.1021/ja027175o