2'-deoxy-2'-(tert-butylthio)adenosine | 603112-50-1

• 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: 2'-deoxy-2'-(tert-butylthio)adenosine
• 英文别名: (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-tert-butylsulfanyl-2-(hydroxymethyl)oxolan-3-ol
• CAS: 603112-50-1
• 化学式: C₁₄H₂₁N₅O₃S
• 分子量: 339.418
• InChiKey: RNDJZUWMGFCEHW-QYVSTXNMSA-N

物化性质

• 沸点：
  640.7±65.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119.31
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-(tert-butylthio)adenosine 在 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 19.0h， 生成 2'-deoxy-2'-(tert-butyldithio)adenosine
  参考文献：
  名称：

  2‘-Mercaptonucleotide Interference Reveals Regions of Close Packing within Folded RNA Molecules

  摘要：

  The 2'-hydroxyl group makes essential contributions to RNA structure and function. As an approach to assess the ability of a mercapto group to serve as a functional analogue for the 2'-hydroxyl group, we synthesized 2'-mercaptonucleotides for use in nucleotide analogue interference mapping. To correlate the observed interference effects with tertiary structure, we used the independently folding DeltaC209 P4-P6 domain from the Tetrahymena group I intron. We generated populations of DeltaC209 P4-P6 molecules containing 2'-mercaptonucleotides located randomly throughout the domain and separated the folded molecules from the unfolded molecules by nondenaturing gel electrophoresis. Iodine-induced cleavage of the RNA molecules revealed the sites at which 2'-mercaptonucleotides interfere with folding. These interferences cluster in the most densely packed regions of the tertiary structure, occurring only at sites that lack the space and flexibility to accommodate a sulfur atom. Interference mapping with 2'-mercaptonucleotides therefore provides a method by which to identify structurally rigid and densely packed regions within folded RNA molecules.

  DOI：

  10.1021/ja035175y
• 作为产物：
  描述：

  6-N-benzoyl-9-<3,5-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)-2-O-trifluoromethanesulfonyl-β-D-arabinofuranosyl>adenine 在 四丁基氟化铵 、 氨 、 四甲基胍 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 18.25h， 生成 2'-deoxy-2'-(tert-butylthio)adenosine
  参考文献：
  名称：

  2‘-Mercaptonucleotide Interference Reveals Regions of Close Packing within Folded RNA Molecules

  摘要：

  The 2'-hydroxyl group makes essential contributions to RNA structure and function. As an approach to assess the ability of a mercapto group to serve as a functional analogue for the 2'-hydroxyl group, we synthesized 2'-mercaptonucleotides for use in nucleotide analogue interference mapping. To correlate the observed interference effects with tertiary structure, we used the independently folding DeltaC209 P4-P6 domain from the Tetrahymena group I intron. We generated populations of DeltaC209 P4-P6 molecules containing 2'-mercaptonucleotides located randomly throughout the domain and separated the folded molecules from the unfolded molecules by nondenaturing gel electrophoresis. Iodine-induced cleavage of the RNA molecules revealed the sites at which 2'-mercaptonucleotides interfere with folding. These interferences cluster in the most densely packed regions of the tertiary structure, occurring only at sites that lack the space and flexibility to accommodate a sulfur atom. Interference mapping with 2'-mercaptonucleotides therefore provides a method by which to identify structurally rigid and densely packed regions within folded RNA molecules.

  DOI：

  10.1021/ja035175y