5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2-[tris-N,N',N''-trifluoroacetamido-(3,9,13-triazatridecyl])-2'-deoxyguanosine | 259141-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2-[tris-N,N',N''-trifluoroacetamido-(3,9,13-triazatridecyl])-2'-deoxyguanosine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-6-O-(4-nitrophenylethyl)-2-N-[tris(N,N',N''-trifluoroacetyl)-4,9,13-triazatridecane-1-yl]-2'-deoxyguanosine
• CAS: 259141-10-1
• 化学式: C₅₅H₅₈F₉N₉O₁₁
• 分子量: 1192.1
• InChiKey: PVKYWZVOBLCIPQ-HHWNUHTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.46
• 重原子数：
  84.0
• 可旋转键数：
  28.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  234.87
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2-[tris-N,N',N''-trifluoroacetamido-(3,9,13-triazatridecyl])-2'-deoxyguanosine 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2-[tris-N,N',N''-trifluoroacetamido-(3,9,13-triazatridecyl)]-2'-deoxyguanosine-3'-O-(2-cyanoethyl-N,N-diisopropyl) phosphoramidite
  参考文献：
  名称：

  Synthesis and Hybridization Properties of Oligonucleotides Containing Polyamines at the C-2 Position of Purines: A Pre-synthetic Approach for the Incorporation of Spermine into Oligodeoxynucleotides Containing 2-(4,9,13-Triazatridecyl)-2′-deoxyguanosine

  摘要：

  We have developed a synthesis of spermine-containing oligonucleotides (ODN-sper) which allows incorporation of multiple polyamine residues. This approach was based on the pertrifluoroacetylated 5'DMT-dGsper phosphoramidite synthon. Its coupling yield with resin-bound ODN decreased dramatically when close to the 3'-end. Optimization of the coupling conditions allowed 22-mer ODNs containing up to six spermine residues to be synthesized. Several ODNs of different sequences with 1-4 pendent spermines could be purified and their hybridization properties were evaluated. Duplex melting temperatures increased linearly with the number of polyamine.residues (DeltaT(m)/sper = 3.0 +/- 0.2 degreesC in 100 mM NaCl). This compares very favorably with values reported for duplexes of similar initial stability containing other cation-substituted bases. Moreover, the stability increase was neither sequence nor position-dependent, and even contiguous spermine residues did not crosstalk. Extrapolation based on these findings leads to the conclusion that a duplex formed with a 22-mer oligonucleotide containing seven spermine residues would be as stable as genomic DNA, which highlights its potential for DNA strand invasion.

  DOI：

  10.1002/1521-3765(20001117)6:22<4188::aid-chem4188>3.0.co;2-n
• 作为产物：
  描述：

  3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine 在 吡啶 、 triethylamine tris(hydrogen fluoride) 、 四甲基胍 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 58.0h， 生成 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2-[tris-N,N',N''-trifluoroacetamido-(3,9,13-triazatridecyl])-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis and Hybridization Properties of Oligonucleotides Containing Polyamines at the C-2 Position of Purines: A Pre-synthetic Approach for the Incorporation of Spermine into Oligodeoxynucleotides Containing 2-(4,9,13-Triazatridecyl)-2′-deoxyguanosine

  摘要：

  We have developed a synthesis of spermine-containing oligonucleotides (ODN-sper) which allows incorporation of multiple polyamine residues. This approach was based on the pertrifluoroacetylated 5'DMT-dGsper phosphoramidite synthon. Its coupling yield with resin-bound ODN decreased dramatically when close to the 3'-end. Optimization of the coupling conditions allowed 22-mer ODNs containing up to six spermine residues to be synthesized. Several ODNs of different sequences with 1-4 pendent spermines could be purified and their hybridization properties were evaluated. Duplex melting temperatures increased linearly with the number of polyamine.residues (DeltaT(m)/sper = 3.0 +/- 0.2 degreesC in 100 mM NaCl). This compares very favorably with values reported for duplexes of similar initial stability containing other cation-substituted bases. Moreover, the stability increase was neither sequence nor position-dependent, and even contiguous spermine residues did not crosstalk. Extrapolation based on these findings leads to the conclusion that a duplex formed with a 22-mer oligonucleotide containing seven spermine residues would be as stable as genomic DNA, which highlights its potential for DNA strand invasion.

  DOI：

  10.1002/1521-3765(20001117)6:22<4188::aid-chem4188>3.0.co;2-n

文献信息

• Synthetic Oligonucleotide Combinatorial Libraries. 3. Synthesis of Polyamevonucleosides
  作者：Przemyslaw Godzina、Katarzyna Adrych-Rozek、Wojciech T. Markiewicz

  DOI：10.1080/07328319908044615

  日期：1999.11

  Synthesis of polyamino-2'-deoxynucleosides was studied. A synthesis of 2'-deoxyadenosine and 2'-deoxyguanosine derivatives carrying a protected spermine moiety at N-6 and N-2 positions respectively is described using unprotected polyamines as substrates. The question of reactivity of primary and secondary amino groups present in polyamines was studied. The evidence that only primary amino groups react with the synthesised precursors was accomplished from experiments with a secondary amine (di-n-butylamine). An approach to analyse properties of polyaminooligonucleotides using their synthetic combinatorial libraries is discussed.