methyl 5-(2'-deoxy-β-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate | 289712-89-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: methyl 5-(2'-deoxy-β-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate
• 英文别名: methyl 2'-deoxypseudouridine-1-propanoate；methyl 3-[5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-1-yl]propanoate
• CAS: 289712-89-6
• 化学式: C₁₃H₁₈N₂O₇
• 分子量: 314.295
• InChiKey: ZYNQVVLYTHURHI-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5-(2'-deoxy-β-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 在 吡啶 作用下， 以 异丙醇 为溶剂， 反应 53.0h， 生成 N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide
  参考文献：
  名称：

  摘要：

  The 2'-deoxypseudouridine (5) was functionalized at N(1) with methyl acrylate by Michael addition. The resulting methyl 2'-deoxypseudouridine-1-propanoate (6) was converted to the phosphoramidite 8 and to the amino-functionalized derivative 9, which was transformed into the fluorescein-labeled phosphoramidites 14 and 16. Fluorescent oligonucleotides were synthesized either from these building blocks or by post-synthetic modification of oligomers containing 2'-deoxypseudouridine subunits. The stability of oligonucleotide duplexes was determined from the melting profiles, measured by UV- or VIS-light absorbance, as well as from the fluorescence emission spectra. While small spacer residues did not affect the thermal stability of the 2'-deoxypseudouridine-containing duplexes, large dye residues led to destabilization.

  DOI：

  10.1002/1522-2675(20000607)83:6<1108::aid-hlca1108>3.0.co;2-9
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 脱氧假尿苷 在 三乙基碳酸氢铵缓冲液 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以89%的产率得到methyl 5-(2'-deoxy-β-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate
  参考文献：
  名称：

  摘要：

  The 2'-deoxypseudouridine (5) was functionalized at N(1) with methyl acrylate by Michael addition. The resulting methyl 2'-deoxypseudouridine-1-propanoate (6) was converted to the phosphoramidite 8 and to the amino-functionalized derivative 9, which was transformed into the fluorescein-labeled phosphoramidites 14 and 16. Fluorescent oligonucleotides were synthesized either from these building blocks or by post-synthetic modification of oligomers containing 2'-deoxypseudouridine subunits. The stability of oligonucleotide duplexes was determined from the melting profiles, measured by UV- or VIS-light absorbance, as well as from the fluorescence emission spectra. While small spacer residues did not affect the thermal stability of the 2'-deoxypseudouridine-containing duplexes, large dye residues led to destabilization.

  DOI：

  10.1002/1522-2675(20000607)83:6<1108::aid-hlca1108>3.0.co;2-9