thymidine(3',5')thymidine hydroxymethylphosphonate

• 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: thymidine(3',5')thymidine hydroxymethylphosphonate
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-[[hydroxymethyl-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphoryl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₂₁H₂₉N₄O₁₂P
• 分子量: 560.455
• InChiKey: TUYAHXPRQGUGKT-UGHUSNSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  214
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3'-O-acetylthymidine 在 N-甲基咪唑 、 2,4,6-三甲基吡啶 、 ammonium hydroxide 、 溶剂黄146 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.75h， 生成 thymidine(3',5')thymidine hydroxymethylphosphonate
  参考文献：
  名称：

  Hydroxymethylphosphonate: Novel Oligonucleotide Analogue

  摘要：

  Thymidine(3',5')thymidine hydroxymethylphosphonate (10), the first oligonucleotide bearing hydroxymethylphosphonate function, and t-butylammonium 5'-O-monomethoxytritylthymidine 3'-O-acetoxymethylphosphonate (7), oligonucleotide monomer, were synthesized using t-butylammonium O-methylacetoxymethylphosphonate (4) as a novel phosphonylating agent. Hydroxymethylphosphonate internucleotide linkage is stable at physiological pH and resistant to 3'- and 5'-exonucleases. While retaining the neutral character of the phosphonate modification, the presence of hydroxymethyl function increases hydrophilicity of hydroxymethylphosphonate oligonucleotide and its solubility in water compared to the parent methylphosphonate analogue. Therefore, hydroxymethylphosphonate modification can be used to fine-tune the physicochemical properties of antisense oligonucleotides. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1011

文献信息

• Chemical synthesis of oligothymidylate having hydroxymethylphosphonate internucleotidic linkages
  作者：Takeshi Wada、Mitsuo Sekine

  DOI：10.1016/0040-4039(95)01890-t

  日期：1995.11

  A new type of non-ionic DNA analogues bearing hydroxymethylphosphonate internucleotidic linkages (HMP-DNA) were synthesized in good yields. A dimer having the hydroxymethylphosphonate linkage was synthesized from the corresponding H-phosphonate via a trimethylsilyl phosphite intermediate. This method was applied to the solid-phase synthesis of a decathymidylate having hydroxymethylphosphonate internucleotidic linkages.