[(2R,3S,5R)-3-acetyloxy-5-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)oxolan-2-yl]methyl acetate | 500361-27-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,5R)-3-acetyloxy-5-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 500361-27-3
• 化学式: C₁₅H₁₉NO₇
• 分子量: 325.318
• InChiKey: OVNMYTDSKQJWEC-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)oxolan-2-yl]methyl acetate 在 28percent aq. NH₄OH 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到3-Hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-methyl-1H-pyridin-4-one
  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：

  3-苄氧基-2-甲基-4(1H)-吡啶酮 在 palladium on activated charcoal 硫酸氢铵 、 氢气 、 六甲基二硅氮烷 作用下， 以 乙酸乙酯 为溶剂， 反应 28.0h， 生成 [(2R,3S,5R)-3-acetyloxy-5-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)oxolan-2-yl]methyl acetate
  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

文献信息

• Soft Metal-Mediated Base Pairing with Novel Synthetic Nucleosides Possessing an <i>O</i>,<i>S</i>-Donor Ligand
  作者：Yusuke Takezawa、Kentaro Tanaka、Maiko Yori、Shohei Tashiro、Motoo Shiro、Mitsuhiko Shionoya

  DOI：10.1021/jo800587d

  日期：2008.8.1

  Metal-mediated base pairing with artificial ligand-bearing nucleosides allows site-selective metal incorporation inside DNA duplexes. In particular, this strategy has provided a general way of discrete, heterogeneous metal arrays in a programmable manner. To increase the kind of metallo-building blocks, we have newly synthesized two artificial nucleosides which have an O,S-donor ligand as the nucleobase moiety, mercaptopyridone (M) and hydroxypyridinethione (S). These nucleosides were found to efficiently form metal-mediated base pairs with soft transition metal ions such as Pd2+ and Pt2+.