((2R,3S,5R)-3-(4-methylbenzoyloxy)-5-(2-oxo-2,3-dihydro-1H-perimidin-1-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate | 938453-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ((2R,3S,5R)-3-(4-methylbenzoyloxy)-5-(2-oxo-2,3-dihydro-1H-perimidin-1-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate
• 英文别名: ((2R,3R,5R)-3-(4-methylbenzyloxy)-5-(2-oxo-2,3-dihydro-1H-perimidin-1yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate；[(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-(2-oxo-3H-perimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 938453-07-7
• 化学式: C₃₂H₂₈N₂O₆
• 分子量: 536.584
• InChiKey: PDGMFLDTFRBWTB-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((2R,3S,5R)-3-(4-methylbenzoyloxy)-5-(2-oxo-2,3-dihydro-1H-perimidin-1-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-perimidin-2(3H)-one
  参考文献：
  名称：

  氢键键合或堆叠相互作用，以区分含烷基化DNA的合成核苷探针的寡核苷酸的双链体稳定性。

  摘要：

  与修饰的DNA杂交的寡核苷酸是有用的化学工具，用于探测稳定DNA双链体的非共价相互作用。为了更好地理解影响杂交探针对O 6烷基鸟嘌呤损伤特异性的相互作用，我们就稳定由天然氨基酸组成的双链DNA的能力研究了一系列合成核苷类似物（BIM，Benzi和Peri）。或损坏的DNA寡核苷酸。碱基修饰的核苷类似物包含系统变化的氢键和π堆积性质。将核苷探针掺入DNA中并配对相反的规范碱基（A，T，C或G），O 6-甲基鸟嘌呤（O 6 -MeG），O6-苄基鸟嘌呤（O 6 -BnG）或稳定的无碱基位点类似物（四氢呋喃，THF）。根据双链体形成的自由能，当将Peri与O 6- MeG配对时，观察到最高的稳定度。热力学数据表明，较小的探针通过氢键使DNA双链体更稳定，而对π堆栈具有更大容量的较大的探针在碱基堆积的基础上对双链体的稳定做出了更大的贡献。这些结果表明，当BIM，Benzi或Peri与相反的含损伤DNA而不是未修饰的DNA（即O

  DOI：

  10.1002/chem.201204593
• 作为产物：
  描述：

  1,8-二氨基萘 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 ((2R,3S,5R)-3-(4-methylbenzoyloxy)-5-(2-oxo-2,3-dihydro-1H-perimidin-1-yl)tetrahydrofuran-2-yl)methyl 4-methylbenzoate
  参考文献：
  名称：

  A Synthetic Nucleoside Probe that Discerns a DNA Adduct from Unmodified DNA

  摘要：

  Selective pairing of engineering nucleosides in DNA duplexes provides a potential means to probe structurally modified DNA bases (i.e., DNA adducts) and address challenges associated with correlating adduct chemical structure with biological impact. The current study provides the first example of a thermodynamically stable DNA base pair that is comprised of a biologically relevant carcinogen-DNA adduct and a synthetic nucleoside probe. O-6-Benzylguanine is a mutagenic DNA adduct; molecular modeling indicates that a novel diaminonaphthyl-derived nucleoside (dNap):O-6-benzylguanine base pair may be stabilized by a combination of hydrogen-bonding and hydrophobic interactions. The nucleoside dNap was synthetically incorporated into oligonucleotides, and a series of duplexes were evaluated by thermal denaturation studies. The bulky DNA adduct O-6-benzylguanine forms a highly stable and orthogonal base pair with dNap. Data indicate pi-stacking potential, self-pairing capacity, isomeric selectivity, 1:1 duplex stoichiometry, and a B-form DNA structure. Further studies are required to understand the physical determinants of adduct:probe pair stability for the design of probes for diverse forms of DNA damage and for the development of adduct-probe-based molecular techniques.

  DOI：

  10.1021/ja070688g