9-(3',5'-O-tetraisopropyldisiloxane-1,3-diyl-β-D-ribofuranosyl)purine | 133324-30-8

• 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: 9-(3',5'-O-tetraisopropyldisiloxane-1,3-diyl-β-D-ribofuranosyl)purine
• 英文别名: (6aR,8R,9R,9aS)-2,2,4,4-tetra(propan-2-yl)-8-purin-9-yl-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 133324-30-8
• 化学式: C₂₂H₃₈N₄O₅Si₂
• 分子量: 494.739
• InChiKey: VONZXLQMSFBCPD-NXLVEIQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(3',5'-O-tetraisopropyldisiloxane-1,3-diyl-β-D-ribofuranosyl)purine 在 吡啶 、 对甲苯磺酸 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 9-(2'-O-tetrahydropyranyl-5'-O-(dimethoxytrityl)-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：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 9 - (Β-D -呋喃核糖)嘌呤 在 吡啶 作用下， 反应 2.0h， 生成 9-(3',5'-O-tetraisopropyldisiloxane-1,3-diyl-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

文献信息

• Functional group substitutions as probes of hydrogen bonding between GA mismatches in RNA internal loops
  作者：John SantaLucia、Ryszard Kierzek、Douglas H. Turner

  DOI：10.1021/ja00011a039

  日期：1991.5

  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.