5-[N-(4-trifluoroacetylaminobutyl)]carbamoylmethyl-2'-deoxyuridine | 208758-77-4

• 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: 5-[N-(4-trifluoroacetylaminobutyl)]carbamoylmethyl-2'-deoxyuridine
• CAS: 208758-77-4
• 化学式: C₁₇H₂₃F₃N₄O₇
• 分子量: 452.387
• InChiKey: NAHHPGJVIPMHCW-DMDPSCGWSA-N

物化性质

• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.71
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  162.75
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-[N-(4-trifluoroacetylaminobutyl)]carbamoylmethyl-2'-deoxyuridine 在 ammonium hydroxide 、 苯酚 作用下， 反应 5.0h， 生成 N-[4-(Acridin-9-ylamino)-butyl]-2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide
  参考文献：
  名称：

  Effect of Acridine with Various Linker Arms Attached to C5 Position of 2′-Deoxyuridine on the Stability of DNA/DNA and DNA/RNA Duplexes

  摘要：

  Acridine-modified oligodeoxyribonucleotides (ODNs) at the CS-position of a 2'-deoxyuridine via different lengths of linker arms were synthesized. Reaction of 5-(N-aminoalkyl)carbamoylmethyl-2'-deoxyuridines with 9-phenoxyacridine gave the acridine-modified 2'-deoxyuridines which were incorporated into ODNs. The duplexes containing the acridine-modified strands and their complementary DNA or RNA were thermally more stable than that containing the unmodified strand. Thermal stability of the duplexes of the modified ODNs varied depending on the length of the linker arms.

  DOI：

  10.1080/07328319808003463
• 作为产物：
  描述：

  三氟乙酸乙酯 、 N-(4-Amino-butyl)-2-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide 在 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 生成 5-[N-(4-trifluoroacetylaminobutyl)]carbamoylmethyl-2'-deoxyuridine
  参考文献：
  名称：

  Effect of Acridine with Various Linker Arms Attached to C5 Position of 2′-Deoxyuridine on the Stability of DNA/DNA and DNA/RNA Duplexes

  摘要：

  Acridine-modified oligodeoxyribonucleotides (ODNs) at the CS-position of a 2'-deoxyuridine via different lengths of linker arms were synthesized. Reaction of 5-(N-aminoalkyl)carbamoylmethyl-2'-deoxyuridines with 9-phenoxyacridine gave the acridine-modified 2'-deoxyuridines which were incorporated into ODNs. The duplexes containing the acridine-modified strands and their complementary DNA or RNA were thermally more stable than that containing the unmodified strand. Thermal stability of the duplexes of the modified ODNs varied depending on the length of the linker arms.

  DOI：

  10.1080/07328319808003463

文献信息

• Effect of the Terminal Amino Group of a Linker Arm and Its Length at the C5 Position of a Pyrimidine Nucleoside on the Thermal Stability of DNA Duplexes
  作者：Hiroaki Ozaki、Masayuki Mine、Yoshinori Ogawa、Hiroaki Sawai

  DOI：10.1006/bioo.2001.1212

  日期：2001.8

  different chain length and a different functional group (methyl or amino), were synthesized and incorporated into oligodeoxyribonucleotides. The effect of the substituent groups in the major groove on the stability of the duplexes was investigated by UV melting experiments. It was found that the stabilization of these duplexes by a terminal amino group depended on the length of a linker arm.

  合成了在C5-位带有取代基的2'-脱氧尿苷衍生物，其具有不同的链长和不同的官能团（甲基或氨基），并掺入到寡脱氧核糖核苷酸中。通过紫外熔融实验研究了主凹槽中取代基对双链体稳定性的影响。发现末端氨基对这些双链体的稳定取决于连接臂的长度。