N6-benzoyl-5'-O-<4,4'-dimethoxytrityl-8-amino(2-aminoethyl)>-2'-deoxyadenosine | 151203-55-3

• 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: N6-benzoyl-5'-O-<4,4'-dimethoxytrityl-8-amino(2-aminoethyl)>-2'-deoxyadenosine
• 英文别名: N⁶-benzoyl-5'-O-<4,4'-dimethoxytrityl-8-amino(2-aminoethyl)>-2'-deoxyadenosine；N⁶-benzoyl-5'-O-[4,4'-dimethoxytrityl-8-amino(2-aminoethyl)]-2'-deoxyadenosine
• CAS: 151203-55-3
• 化学式: C₄₀H₄₁N₇O₆
• 分子量: 715.809
• InChiKey: KUQKWHMBZJCGML-LBFZIJHGSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  167.9
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N6-benzoyl-5'-O-<4,4'-dimethoxytrityl-8-amino(2-aminoethyl)>-2'-deoxyadenosine 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 14.5h， 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：

  N-[8-bromo-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 N6-benzoyl-5'-O-<4,4'-dimethoxytrityl-8-amino(2-aminoethyl)>-2'-deoxyadenosine
  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

• Influence of Linker Length on Ligase‐Catalyzed Oligonucleotide Polymerization
  作者：Chun Guo、Yasaman Mahdavi‐Amiri、Ryan Hili

  DOI：10.1002/cbic.201800616

  日期：2019.3.15

  Ligase-catalyzed oligonucleotide polymerization (LOOPER) that enables the sequence-defined generation of DNA with up to 16 different modifications has recently been developed. This approach was used to develop new classes of diversely modified DNA aptamers for molecular recognition through in vitro evolution. The modifications in LOOPER are appended by use of a long hexane-1,6-diamine linker, which

  最近开发了连接酶催化的寡核苷酸聚合（LOOPER），该序列可实现具有多达16种不同修饰的DNA序列定义的生成。这种方法被用来开发新的一类多样化修饰的DNA适体，用于通过体外进化进行分子识别。LOOPER中的修饰是通过使用长己烷-1,6-二胺连接基附加的，这可能会对结合热力学产生负面影响。在这里，我们探索了借助较短的接头引入修饰的方法，以及使用市售亚磷酰胺的方法，并评估了它们的结合效率和保真度。我们观察到，较短的接头在LOOPER期间的耐受性较低，而非常短的接头会提供较高水平的错误和序列偏倚。发现乙烷-1,2-二胺连接基在收率方面是最佳的，效率和偏见；然而，密码子调整是必要的。LOOPER的这种较短连接子的反密码子集在探索各种化学修饰对DNA分子功能的影响方面应被证明是有价值的。