1’-(3’-O-tertbutyldimethylsilyl-5’-O-triisopropylsilyl-2’-deoxy-β-D-ribofuranoside)-6-bromoquinazoline-2,4-(3H)-dione | 1433812-19-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1’-(3’-O-tertbutyldimethylsilyl-5’-O-triisopropylsilyl-2’-deoxy-β-D-ribofuranoside)-6-bromoquinazoline-2,4-(3H)-dione
• 英文别名: 1’-(3’-O-tertbutyldimethylsilyl-5’-O-triisopropylsilyl-2’-deoxy-β-D-ribofuranoside)-6-bromoquinazoline- 2,4-(3H)-dione
• CAS: 1433812-19-1
• 化学式: C₂₈H₄₇BrN₂O₅Si₂
• 分子量: 627.767
• InChiKey: HDPPMQPPUXRTOU-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1’-(3’-O-tertbutyldimethylsilyl-5’-O-triisopropylsilyl-2’-deoxy-β-D-ribofuranoside)-6-bromoquinazoline-2,4-(3H)-dione 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四丁基氟化铵 、 potassium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 1’-(2’-deoxy-β-D-ribofuranoside)-6-(4-methoxy)phenylquinazoline-2,4-(3H)-dione
  参考文献：
  名称：

  Synthesis and Solvatochromic Fluorescence of Biaryl Pyrimidine Nucleosides

  摘要：

  Fluorescent pyrimidine analogs containing a fused biphenyl unit were prepared in high yields using stereoselective N-glycosylation and Suzuki-Miyaura cross-coupling reactions. The resulting "push-pull" fluorophores exhibit highly solvatochromic emissions from twisted intramolecular charge-transfer (TICT) states.

  DOI：

  10.1021/ol400930s
• 作为产物：
  描述：

  6-溴喹唑啉-2,4-二酮 在 咪唑 、 N,O-双三甲硅基乙酰胺 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.49h， 生成 1’-(3’-O-tertbutyldimethylsilyl-5’-O-triisopropylsilyl-2’-deoxy-β-D-ribofuranoside)-6-bromoquinazoline-2,4-(3H)-dione
  参考文献：
  名称：

  A Highly Fluorescent Nucleobase Molecular Rotor

  摘要：

  Fluorescent base analogs (FBAs) are powerful probes of nucleic acids' structures and dynamics. However, previously reported FBAs exhibit relatively low brightness and therefore limited sensitivity of detection. Here we report the hitherto brightest FBA that has ideal molecular rotor properties for detecting local dynamic motions associated with base pair mismatches. The new trans-stilbene annulated uracil derivative "T-ts" exhibits bright fluorescence emissions in various solvents (epsilon x Phi = 3400-29 700 cm(-1) M-1) and is highly sensitive to mechanical motions in duplex DNA (epsilon x Phi = 150-4250 cm(-1) M-1). T-ts is thereby a "smart" thymidine analog, exhibiting a 28-fold brighter fluorescence intensity when base paired with A as compared to T or C. Time-correlated single photon counting revealed that the fluorescence lifetime of T-t(s) (tau = 4-11 ns) was shorter than its anisotropy decay in well-matched duplex DNA (theta = 20 ns), yet longer than the dynamic motions of base pair mismatches (0.1-10 ns). These properties enable unprecedented sensitivity in detecting local dynamics of nucleic acids.

  DOI：

  10.1021/jacs.0c05180

文献信息

• Fluorescent Probe for Proton-Coupled DNA Folding Revealing Slow Exchange of <i>i</i>-Motif and Duplex Structures
  作者：Guillaume Mata、Nathan W. Luedtke

  DOI：10.1021/ja508741u

  日期：2015.1.21

  proton-coupled DNA folding, we developed a "push-pull" fluorescent nucleoside analog composed of dimethylaniline (DMA) fused to deoxycytidine. "(DMA)C" exhibits the same pKa and base pairing characteristics as native cytosine residues in the human telomeric repeat sequence, where it causes little or no perturbation of DNA structure or stability. Upon protonation of (DMA)C, enhanced charge transfer results in

  电离核碱基参与沃森和克里克规则之外的配对相互作用。碱基配对和电离可以通过整体构象变化进行耦合，以将质子化核碱基的表观 pKa 值提高到高于生理 pH 值。为了提供质子耦合 DNA 折叠的第一个特定报告器，我们开发了一种“推拉”荧光核苷类似物，由与脱氧胞苷融合的二甲基苯胺 (DMA) 组成。“(DMA)C”表现出与人类端粒重复序列中的天然胞嘧啶残基相同的 pKa 和碱基配对特征，其中它对 DNA 结构或稳定性几乎没有或没有干扰。(DMA)C 质子化后，增强的电荷转移导致其激发/发射最大值发生大的红移 (+40 nm)。(DMA)C 的荧光强度、各向异性、能量转移特性可用于实时跟踪构象变化。通过将含有 5' 单链悬垂的 (DMA) C 标记双链体与过量的未标记 DNA 混合以启动热力学有利的展开-重折叠反应，从其互补物中释放 (DMA) C 标记的链，从而进行链置换试验。添加 i-motif DNA