N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)-O6-(2''',4''',6'''-triisopropylphenylsulfonyl)guanosine | 133324-34-2

• 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: N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)-O6-(2''',4''',6'''-triisopropylphenylsulfonyl)guanosine
• 英文别名: N²-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)-O⁶-(2''',4''',6'''-triisopropylphenylsulfonyl)guanosine；2-N-isobutyryl-2',3',5'-tri-O-isobutyryl-6-O-(2,4,6-triisopropylbenzenesulfonyl)guanosine
• CAS: 133324-34-2
• 化学式: C₄₁H₅₉N₅O₁₁S
• 分子量: 830.012
• InChiKey: WJCIGPSEUQXHRM-JEQJLXBKSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  58.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  204.2
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  异丁酸酐 、 N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)-O6-(2''',4''',6'''-triisopropylphenylsulfonyl)guanosine 在 4-二甲氨基吡啶 、 三乙胺 、 肼 作用下， 生成 2-isobutyramido-6-(2-isobutyrylhydrazino)-9-(2',3',5'-tri-O-isopropyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Functional group substitutions as probes of hydrogen bonding between GA mismatches in RNA internal loops

  摘要：

  The contribution of hydrogen bonding to the stability of GA mismatches in RNA is investigated by making functional group substitutions. Such substitutions are made possible by the chemical synthesis of RNA; chemical incorporation of purine riboside and 2-aminopurine riboside into oligoribonucleotides is reported. In particular, replacing the 6-amino groups of internal loop adenosines with hydrogen atoms in (rGCGAGCG)2, (rGGCGAGCC)2, (rGCAGGCG)2, and (rCGCAGGCG)2 destabilizes the duplexes by 2.8, 3.0, 3.2, and 2.7 kcal/mol, respectively. The results suggest hydrogen bonding within each GA mismatch contributes at least -1.4 kcal/mol to duplex stability. Results on control sequences in which the internal loop residues are changed to inosine, 2-aminopurine riboside, or purine riboside are consistent with this interpretation. The results provide insight into the source of the unusual stability of RNA duplexes with internal loops containing GA mismatches (Santa Lucia, J., Jr.; Kierzek, R.; Turner, D. H. Biochemistry 1990, 29, 8813-8819). In contrast to GA mismatches in internal loops, hydrogen bonding between GA mismatches at the ends of oligonucleotide helices does not make a large contribution to helix stability. The implications of these results for predicting RNA structure are discussed.

  DOI：

  10.1021/ja00011a039
• 作为产物：
  描述：

  鸟苷 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 氯仿 为溶剂， 反应 44.0h， 生成 N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)-O6-(2''',4''',6'''-triisopropylphenylsulfonyl)guanosine
  参考文献：
  名称：

  Functional group substitutions as probes of hydrogen bonding between GA mismatches in RNA internal loops

  摘要：

  The contribution of hydrogen bonding to the stability of GA mismatches in RNA is investigated by making functional group substitutions. Such substitutions are made possible by the chemical synthesis of RNA; chemical incorporation of purine riboside and 2-aminopurine riboside into oligoribonucleotides is reported. In particular, replacing the 6-amino groups of internal loop adenosines with hydrogen atoms in (rGCGAGCG)2, (rGGCGAGCC)2, (rGCAGGCG)2, and (rCGCAGGCG)2 destabilizes the duplexes by 2.8, 3.0, 3.2, and 2.7 kcal/mol, respectively. The results suggest hydrogen bonding within each GA mismatch contributes at least -1.4 kcal/mol to duplex stability. Results on control sequences in which the internal loop residues are changed to inosine, 2-aminopurine riboside, or purine riboside are consistent with this interpretation. The results provide insight into the source of the unusual stability of RNA duplexes with internal loops containing GA mismatches (Santa Lucia, J., Jr.; Kierzek, R.; Turner, D. H. Biochemistry 1990, 29, 8813-8819). In contrast to GA mismatches in internal loops, hydrogen bonding between GA mismatches at the ends of oligonucleotide helices does not make a large contribution to helix stability. The implications of these results for predicting RNA structure are discussed.

  DOI：

  10.1021/ja00011a039

文献信息

• Biosynthetic Production of [<i>N</i>²,1,3,7,9-¹⁵N]Guanosine and [1,3,7,9-¹⁵N]inosine and conversion into [<i>N</i>⁶,1,3,7,9-¹⁵N]adenosine for structure elucidation of RNA by heteronuclear NMR
  作者：Annette C. Niemann、Mónica Meyer、Thomas Engeloch、Oliver Botta、Alfons Hädener、Peter Strazewski

  DOI：10.1002/hlca.19950780213

  日期：1995.3.22

  A procedure was developed for the biosynthetic preparation of 15N-labelled guanosine and inosine through the action of a mutant Bacillus subtilis strain. Crude [N2,1,3,7,9-15N]guanosine and [1,3,7,9-15N]inosine were isolated from the culture filtrate by precipitation and anion-exchange chromatography (Scheme 1). No cell lysis and no enzymatic degradation was necessary. The per-isobutyrylated derivatives

  通过突变枯草芽孢杆菌菌株的作用，开发了一种生物合成制备15 N标记的鸟苷和肌苷的程序。粗[ Ñ 2，1,3,7,9- 15 N]鸟苷和[1,3,7,9- 15 N]肌苷从通过沉淀和阴离子交换层析（培养滤液中分离方案1）。无需细胞裂解，也无需酶促降解。全异丁酰化衍生物1和2从复杂的混合物中分离纯化产物，通过不同的亲脂性对其进行纯化，然后分三步进行分离，包括正相和反相硅胶色谱法。一升复杂的营养培养基可产生8.44 mmol的鸟苷衍生物和2.84 mmol的肌苷衍生物，平均富集15 N较高（分别为83.5和91.9原子％）。[ Ñ 6，1,3,7,9- 15 N]腺苷（4）从得到的2'，3'，5'-三ö异丁酰基[1,3,7,9- 15 N]肌苷（1）通过将其1,2,4-三唑基衍生物与15 NH 3水溶液氨解（方案2）。