6N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-(2-(4-imidazolyl)ethylamino)-2'-deoxyadenozine | 151322-48-4

• 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: 6N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-(2-(4-imidazolyl)ethylamino)-2'-deoxyadenozine
• 英文别名: N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-histamino-2'-deoxyadenosine；N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-[2-(imidazol-4-yl)ethylamino]-2'-deoxyadenosine；N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-8-[2-(1H-imidazol-5-yl)ethylamino]purin-6-yl]benzamide
• CAS: 151322-48-4
• 化学式: C₄₃H₄₂N₈O₆
• 分子量: 766.856
• InChiKey: VTHIMOPEGWOKQQ-HKIDPNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  57.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  170.56
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  6N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-(2-(4-imidazolyl)ethylamino)-2'-deoxyadenozine 在 吡啶 、 N-甲基咪唑 、 二氯乙酸 、 mesitylensulphonyl-3-nitrotriazole 作用下， 以 二氯甲烷 为溶剂， 反应 6.08h， 生成
  参考文献：
  名称：

  Synthesis and conformational studies of d(TpA) and r(UpA) conjugated with histamine and ethylenediamine

  摘要：

  Dinucleotides (Figure 1b-d) possessing histamino/ethylenediamino substituents at C8 of adenine have been synthesised for modelling the molecular interactions that occur at catalytic site of nucleases. These compounds have been designed for putative molecular recognition of internucleotide phosphate by a complementary group (imidazole/-NH2) in the pendant C-8 side chains. H-1 NMR spectroscopic analysis of synthesised model compounds indicate that C-8 modification leads to increase in percentage of S conformation of modified sugar while still maintaining an anti glycosyl torsion as in unmodified analog d(TpA). The C-8 side chain functionality (histamine/ethylenediamine) is probably involved in intramolecular interaction (electrostatic/ hydrogen bond) with the phosphate and/or 2'OH in (14). Such predisposition of side chain catalytic groups is important in developing appropriate models for active site of nucleases.

  DOI：

  10.1016/s0040-4020(01)89916-6
• 作为产物：
  描述：

  8-溴-2'-脱氧腺苷 在 吡啶 、 三甲基氯硅烷 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 6N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-(2-(4-imidazolyl)ethylamino)-2'-deoxyadenozine
  参考文献：
  名称：

  Synthesis and conformational studies of d(TpA) and r(UpA) conjugated with histamine and ethylenediamine

  摘要：

  Dinucleotides (Figure 1b-d) possessing histamino/ethylenediamino substituents at C8 of adenine have been synthesised for modelling the molecular interactions that occur at catalytic site of nucleases. These compounds have been designed for putative molecular recognition of internucleotide phosphate by a complementary group (imidazole/-NH2) in the pendant C-8 side chains. H-1 NMR spectroscopic analysis of synthesised model compounds indicate that C-8 modification leads to increase in percentage of S conformation of modified sugar while still maintaining an anti glycosyl torsion as in unmodified analog d(TpA). The C-8 side chain functionality (histamine/ethylenediamine) is probably involved in intramolecular interaction (electrostatic/ hydrogen bond) with the phosphate and/or 2'OH in (14). Such predisposition of side chain catalytic groups is important in developing appropriate models for active site of nucleases.

  DOI：

  10.1016/s0040-4020(01)89916-6

文献信息

• Site-specific functionalization with amino, guanidinium, and imidazolyl groups enabling the activation of 10–23 DNAzyme
  作者：Shanshan Du、Yang Li、Zhilong Chai、Weiguo Shi、Junlin He

  DOI：10.1039/d0ra02226h

  日期：——

  Chemical activation of 10–23 DNAzyme was realized at A9 modified with active functional groups amino, guanidinium, and imidazolyl groups.

  10-23 DNAzyme的化学激活是通过在A9上修饰活性官能团氨基、胍基和咪唑基实现的。
• INCORPORATION OF 8-HISTAMINYL-DEOXYADENOSINE [8-(2-(4-IMIDAZOLYL)ETHYLAMINO)-2′-DEOXYRIBOADENOSINE] INTO OLIGODEOXYRIBONUCLEOTIDES BY SOLID PHASE PHOSPHORAMIDITE COUPLING
  作者：Leonard Lermer、John Hobbs、David M. Perrin

  DOI：10.1081/ncn-120015723

  日期：2002.12

  The 3' phosphoramidite of 8-histaminyl deoxyadenosine has been prepared and successfully incorporated into a short oligodeoxyribonucleotide. The synthetic methodology leading to this preparation is given and the implications for developing new DNAzymes as well as probing unusual nucleic acid structures are discussed.