2'-deoxy-2'-(2-nitrophenyldithio)guanosine | 603112-58-9

• 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'-(2-nitrophenyldithio)guanosine
• 英文别名: 2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-[(2-nitrophenyl)disulfanyl]oxolan-2-yl]-1H-purin-6-one
• CAS: 603112-58-9
• 化学式: C₁₆H₁₆N₆O₆S₂
• 分子量: 452.472
• InChiKey: PNCVAAASNHEJCK-PMXXHBEXSA-N

物化性质

• 沸点：
  841.1±75.0 °C(Predicted)
• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  231
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-(2-nitrophenyldithio)guanosine 在 吡啶 、 三氯硫磷 、 Proton Sponge 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.45h， 生成 2'-deoxy-2'-(tert-butyldithio)guanosine-α-thiotriphosphate
  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：

  9-(3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)guanine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 四甲基胍 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.22h， 生成 2'-deoxy-2'-(2-nitrophenyldithio)guanosine
  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