5'-O-(4,4'-dimethoxytrityl)-1,3,2',6',2''',6'''-hexa-N-trifluoroacetylneomycin | 1245704-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6',2''',6'''-hexa-N-trifluoroacetylneomycin
• 英文别名: 5''-O-(dimethoxytrityl)-1,3,2',6',2''',6'''-hexa-N-trifluoroacetylneomycin
• CAS: 1245704-07-7
• 化学式: C₅₆H₅₈F₁₈N₆O₂₁
• 分子量: 1493.08
• InChiKey: YIBJFRQMUKFTFK-UWGIJMTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  101.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  379.05
• 氢给体数：
  12.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-1,3,2',6',2''',6'''-hexa-N-trifluoroacetylneomycin 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成
  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：

  、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 以2.35 g的产率得到5'-O-(4,4'-dimethoxytrityl)-1,3,2',6',2''',6'''-hexa-N-trifluoroacetylneomycin
  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

• Synthesis of Aminoglycoside-3′-Conjugates of 2′-<i>O</i>-Methyl Oligoribonucleotides and Their Invasion to a ¹⁹F labeled HIV-1 TAR Model
  作者：Anu Kiviniemi、Pasi Virta

  DOI：10.1021/bc200101r

  日期：2011.8.17

  The potential of aminoglycosides to induce RNA-invasion has been demonstrated. For this purpose, aminoglycoside-3'-conjugates of 2'-O-methyl oligoribonucleotides have been synthesized entirely on a solid phase. The synthesis includes an automated oligonucleotide chain elongation to solid-supported neomycin, ribostamycin, and methyl neobiosamine, and a two-step deprotection/release of the solid-supported conjugate, which allows exploitation of a simple protecting group scheme. Conjugates have been targeted to a F-19 labeled HIV-1 TAR RNA model (Trans Activation Response element of HIV), which allows monitoring of the invasion by F-19 NMR spectroscopy. A remarkably enhanced invasion, compared to that resulting from the corresponding unmodified 2'-O-methyl oligoribonucleotide (5'-CAGGCUCA-3'), has been obtained by the neomycin conjugate. The increased affinity results from a cooperative binding of the neomycin moiety and hybridization, though the invasion may also follow a mechanism, in which the first molar equivalent of the conjugate induces hybridization of the second.