2-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyloxy)ethyl(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite | 1574642-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyloxy)ethyl(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite
• CAS: 1574642-21-9
• 化学式: C₂₃H₃₈FN₂O₁₀P
• 分子量: 552.534
• InChiKey: UJZANGNOIFNVBE-TXUZVMDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  37.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  142.85
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranosyl bromide 在 N,N-二异丙基乙胺 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 2-(2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-galactopyranosyloxy)ethyl(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y