1,3,2'-tri-N-trifluoroacetylparomamine | 1245704-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2'-tri-N-trifluoroacetylparomamine
• CAS: 1245704-02-2
• 化学式: C₁₈H₂₂F₉N₃O₁₀
• 分子量: 611.372
• InChiKey: PGEIQKHIJZGIDL-HKEUSBCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.92
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  206.91
• 氢给体数：
  8.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,3,2'-tri-N-trifluoroacetylparomamine 在 吡啶 、 二氯乙酸 、 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 C₂₇H₂₉F₁₂N₃O₁₆S
  参考文献：
  名称：

  Solid-Supported Synthesis and Click Conjugation of 4′-C-Alkyne Functionalized Oligodeoxyribonucleotides

  摘要：

  4'-C-[N,N-Di(4-pentyn-l-yl)aminomethyl]thymidine and 4'-C-[N-methyl-N-(4-pentyn-l-yl)aminomethyl]thymidine 3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidites (1, 2) were synthesized, and one or two such monomers were incorporated into a 15-mer oligodeoxyribonucleotide. After chain assembly, azido-functionalized ligands, including appropriate derivatives of 1,4-phenylenedimethaneamine, mannose, paromamine, and neomycin, were conjugated to the alkynyl groups by the click chemistry on a solid support. The influence of the 4'-modifications on the melting temperature with DNA and 2'-O-methyl RNA targets was studied. Oligonucleotides containing one to four mannose ligands in the central part of the chain (up to two 4'-C-[N,N-di(4-pentyn-l-yl)aminomethyl]thymidine units) form equally stable duplexes with complementary 2'-OMe RNA as the corresponding unmodified DNA sequence. At high salt content, the mannose conjugation is even stabilizing. On using a DNA target, a modest destabilization occurs. All the amino group bearing conjugates stabilized the duplexes, the DNA.DNA duplexes more than the DNA.2'-O-methyl RNA duplexes.

  DOI：

  10.1021/bc100268w
• 作为产物：
  描述：

  三氟乙酸甲酯 、 paromamine sulfate 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以76%的产率得到1,3,2'-tri-N-trifluoroacetylparomamine
  参考文献：
  名称：

  Solid-Supported Synthesis and Click Conjugation of 4′-C-Alkyne Functionalized Oligodeoxyribonucleotides

  摘要：

  4'-C-[N,N-Di(4-pentyn-l-yl)aminomethyl]thymidine and 4'-C-[N-methyl-N-(4-pentyn-l-yl)aminomethyl]thymidine 3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidites (1, 2) were synthesized, and one or two such monomers were incorporated into a 15-mer oligodeoxyribonucleotide. After chain assembly, azido-functionalized ligands, including appropriate derivatives of 1,4-phenylenedimethaneamine, mannose, paromamine, and neomycin, were conjugated to the alkynyl groups by the click chemistry on a solid support. The influence of the 4'-modifications on the melting temperature with DNA and 2'-O-methyl RNA targets was studied. Oligonucleotides containing one to four mannose ligands in the central part of the chain (up to two 4'-C-[N,N-di(4-pentyn-l-yl)aminomethyl]thymidine units) form equally stable duplexes with complementary 2'-OMe RNA as the corresponding unmodified DNA sequence. At high salt content, the mannose conjugation is even stabilizing. On using a DNA target, a modest destabilization occurs. All the amino group bearing conjugates stabilized the duplexes, the DNA.DNA duplexes more than the DNA.2'-O-methyl RNA duplexes.

  DOI：

  10.1021/bc100268w