N⁶-benzoyl-8-bromoadenosine | 151322-54-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-benzoyl-8-bromoadenosine
• 英文别名: N-[8-bromo-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 151322-54-2
• 化学式: C₁₇H₁₆BrN₅O₅
• 分子量: 450.249
• InChiKey: LZCPBIBFCJBBDL-UBEDBUPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-8-bromoadenosine 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-8-histaminoadenosine
  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：

  腺苷 在 吡啶 、 三甲基氯硅烷 、 水 、 氢溴酸 、 sodium acetate 作用下， 反应 4.0h， 生成 N⁶-benzoyl-8-bromoadenosine
  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

• Synthesis and conformational studies of d(TpA) and r(UpA) conjugated with histamine and ethylenediamine
  作者：T.P. Prakash、R. Krishna Kumar、K.N. Ganesh

  DOI：10.1016/s0040-4020(01)89916-6

  日期：1993.5

  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.