paromamine sulfate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: paromamine sulfate
• 英文别名: (2R,3S,4R,5R,6S)-5-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-2-(hydroxymethyl)oxane-3,4-diol;sulfuric acid
• 化学式: C₁₂H₂₅N₃O₇*3H₂O₄S
• 分子量: 617.585
• InChiKey: YBTKKYKNONXRFE-SQAHNGQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.73
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  281
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  paromamine sulfate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 6'-O-(4,4-dimethoxytrityl)-5,6,3',4'-tetra-acetyl-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

文献信息

• Solid-Supported Synthesis and Click Conjugation of 4′-<i>C</i>-Alkyne Functionalized Oligodeoxyribonucleotides
  作者：Anu Kiviniemi、Pasi Virta、Harri Lönnberg

  DOI：10.1021/bc100268w

  日期：2010.10.20

  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.