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 | 289712-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 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
• 英文别名: N-(3-aminopropyl)-3-[5-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-1-yl]propanamide
• CAS: 289712-92-1
• 化学式: C₃₆H₄₂N₄O₈
• 分子量: 658.751
• InChiKey: CCHYJKSWZAYAIJ-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-羧基荧光素二硬脂酸酯N-羟基琥珀酰亚胺酯 、 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 以 吡啶 为溶剂， 反应 2.0h， 以56%的产率得到N¹-{3-[({3',6'-bis(2,2-dimethyl-1-oxopropoxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-6-yl}carbonyl)amino]propyl}-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：

  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

文献信息

• ——
  作者：Natalya Ramzaeva、Helmut Rosemeyer、Peter Leonard、Klaus Mühlegger、Frank Bergmann、Herbert von der Eltz、Frank Seela

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

  日期：2000.6.7

  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.