N²-DMF-2-aminothieno[3,4-d]pyrimidine G mimic deoxynucleoside | 1542574-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N²-DMF-2-aminothieno[3,4-d]pyrimidine G mimic deoxynucleoside
• CAS: 1542574-87-7
• 化学式: C₁₄H₁₈N₄O₄S
• 分子量: 338.387
• InChiKey: LHMXEXFJBCWQMJ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.04
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 N²-DMF-2-aminothieno[3,4-d]pyrimidine G mimic deoxynucleoside 在 吡啶 作用下， 反应 16.0h， 以50%的产率得到O5'-(4,4’-dimethoxytrityl)-N2-(dimethylformamidine)-2-aminothieno[3,4-d]pyrimidine
  参考文献：
  名称：

  Conquering 2-Aminopurine’s Deficiencies: Highly Emissive Isomorphic Guanosine Surrogate Faithfully Monitors Guanosine Conformation and Dynamics in DNA

  摘要：

  The archetypical fluorescent nucleoside. analog, 2-aminopurine (2Ap), has been used in countless assays, though it suffers from very low quantum, yield, especially when included in double strands, and from the fact that its residual emission frequently does not represent biologically relevant conformations. To, conquer 2Ap's,deficiencies, deoxythienoguanosine (dh-G) was recently,developed. Here, steady-state and time-resolved fluorescence spectroscopy was used to compare the ability of 2Ap and dthG, to substitute and provide relevant structural and dynamical information on a key G residue in the () DNA copy of the HIV-1 primer binding site, (-)PBS, both in its stem loop conformation and in the corresponding (-)/(+)PBS duplex. In contrast to 2Ap this fluorescent nucleoside when included in ()PBS or - ()/(+)PBS duplex fully preserves their stability and exhibits a respectable quantum yield and a simple fluorescence decay, with marginal amounts of dark species. In further contrast to 2Ap, the fluorescently detected dthG species reflect the pre-dominantly populated G conformers, which allows exploring their relevant dynamics. Being able to perfectly substitute G residues, dthG will transform nucleic acid biophysics by allowing, for the first time, to selectively and faithfully monitor the conformations and dynamics of a given G residue in a DNA sequence.

  DOI：

  10.1021/ja513107r
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 25.0h， 生成 N²-DMF-2-aminothieno[3,4-d]pyrimidine G mimic deoxynucleoside
  参考文献：
  名称：

  Conquering 2-Aminopurine’s Deficiencies: Highly Emissive Isomorphic Guanosine Surrogate Faithfully Monitors Guanosine Conformation and Dynamics in DNA

  摘要：

  The archetypical fluorescent nucleoside. analog, 2-aminopurine (2Ap), has been used in countless assays, though it suffers from very low quantum, yield, especially when included in double strands, and from the fact that its residual emission frequently does not represent biologically relevant conformations. To, conquer 2Ap's,deficiencies, deoxythienoguanosine (dh-G) was recently,developed. Here, steady-state and time-resolved fluorescence spectroscopy was used to compare the ability of 2Ap and dthG, to substitute and provide relevant structural and dynamical information on a key G residue in the () DNA copy of the HIV-1 primer binding site, (-)PBS, both in its stem loop conformation and in the corresponding (-)/(+)PBS duplex. In contrast to 2Ap this fluorescent nucleoside when included in ()PBS or - ()/(+)PBS duplex fully preserves their stability and exhibits a respectable quantum yield and a simple fluorescence decay, with marginal amounts of dark species. In further contrast to 2Ap, the fluorescently detected dthG species reflect the pre-dominantly populated G conformers, which allows exploring their relevant dynamics. Being able to perfectly substitute G residues, dthG will transform nucleic acid biophysics by allowing, for the first time, to selectively and faithfully monitor the conformations and dynamics of a given G residue in a DNA sequence.

  DOI：

  10.1021/ja513107r

文献信息

• Highly emissive deoxyguanosine analogue capable of direct visualization of B–Z transition
  作者：Soyoung Park、Haruka Otomo、Linjie Zheng、Hiroshi Sugiyama

  DOI：10.1039/c3cc48297a

  日期：——

  A 2-aminothieno[3,4-d]pyrimidine G-mimic deoxyribonucleoside, thdG, was synthesized and incorporated readily into oligonucleotides as a versatile fluorescent guanine analogue. We demonstrate that thdG enables the visual detection of Z-DNA successfully based on different π-stacking of B- and Z-DNA.

  我们合成了一种 2-氨基噻吩并[3,4-d]嘧啶 G-模拟脱氧核苷--thdG，并将其作为一种多功能荧光鸟嘌呤类似物轻松地加入到寡核苷酸中。我们证明，thdG 能够成功地根据 B- 和 Z-DNA 的不同 Ï-stacking 对 Z-DNA 进行视觉检测。