1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-2(3H)-one | 1384471-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-benzoimidazol-2(3H)-one；3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-benzimidazol-2-one
• CAS: 1384471-05-9
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: KZBZHBKGTINBGS-HBNTYKKESA-N

物化性质

• 密度：
  1.462±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-2(3H)-one 在 吡啶 、 4-二甲氨基吡啶 、 4-羟基苯并三唑 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.67h， 生成 ((2R,3S,5R)-3-hydroxy-5-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)tetrahydrofuran-2-yl)methyl triphosphate
  参考文献：
  名称：

  Specific Incorporation of an Artificial Nucleotide Opposite a Mutagenic DNA Adduct by a DNA Polymerase

  摘要：

  The ability to detect DNA modification sites at single base resolution could significantly advance studies regarding DNA adduct levels, which are extremely difficult to determine. Artificial nucleotides that are specifically incorporated opposite a modified DNA site offer a potential strategy for detection of such sites by DNA polymerase-based systems. Here we investigate the action of newly synthesized base-modified benzimidazole-derived 2'-deoxynucleoside-5'-O-triphosphates on DNA polymerases when performing translesion DNA synthesis past the pro-mutagenic DNA adduct O-6-benzylguanine (O6-BnG). We found that a mutated form of KlenTaq DNA polymerase, i.e., KTqM747K, catalyzed O6-BnG adduct-specific processing of the artificial BenziTP in favor of the natural dNTPs. Steady-state kinetic parameters revealed that KTqM747K catalysis of BenziTP is 25-fold more efficient for template O-6-BnG than G, and 5-fold more efficient than natural dTMP misincorporation in adduct bypass. Furthermore, the nucleotide analogue BenziTP is required for full-length product formation in O-6-BnG bypass, as without BenziTP the polymerase stalls at the adduct site. By combining the KTqM747K polymerase and BenziTP, a first round of DNA synthesis enabled subsequent amplification of Benzi-containing DNA. These results advance the development of technologies for detecting DNA adducts.

  DOI：

  10.1021/ja5100542
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 50.0 ℃ 、137.9 kPa 条件下， 反应 0.13h， 以85%的产率得到1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  Continuous Flow Photochemistry for the Rapid and Selective Synthesis of 2’-Deoxy and 2’,3’-Dideoxynucleosides

  摘要：

  我们开发了一种新型光化学流动反应器，用于光诱导电子转移脱氧反应，生成 2′-脱氧和 2′,3′-二脱氧核苷。连续流形式极大地提高了反应的效率和选择性，精简的多步骤序列直接提供了非常需要的未受保护的脱氧核苷。

  DOI：

  10.1071/ch12426

文献信息

• Continuous flow photocatalysis enhanced using an aluminum mirror: rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides
  作者：Bo Shen、Matthew W. Bedore、Adam Sniady、Timothy F. Jamison

  DOI：10.1039/c2cc33356b

  日期：——

  reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2'-deoxy and 2',3'-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.

  已经开发出一种具有石英管，铝镜和温度控制装置的独特光化学流反应器，用于光诱导的电子转移脱氧反应，以产生2'-脱氧和2'，3'-二脱氧核苷。连续流形式显着提高了反应的效率和选择性。
• Hydrogen Bonding or Stacking Interactions in Differentiating Duplex Stability in Oligonucleotides Containing Synthetic Nucleoside Probes for Alkylated DNA
  作者：Hailey L. Gahlon、Shana J. Sturla

  DOI：10.1002/chem.201204593

  日期：2013.8.12

  duplex formation, the highest degree of stabilization was observed when Peri was paired opposite O6‐MeG. The thermodynamic data suggest that the smaller probes stabilize DNA duplexes more through hydrogen bonding, whereas the larger probes, with a greater capacity to π stack, contribute to duplex stabilization more on the basis of base stacking. These results demonstrate that increased helix stability

  与修饰的DNA杂交的寡核苷酸是有用的化学工具，用于探测稳定DNA双链体的非共价相互作用。为了更好地理解影响杂交探针对O 6烷基鸟嘌呤损伤特异性的相互作用，我们就稳定由天然氨基酸组成的双链DNA的能力研究了一系列合成核苷类似物（BIM，Benzi和Peri）。或损坏的DNA寡核苷酸。碱基修饰的核苷类似物包含系统变化的氢键和π堆积性质。将核苷探针掺入DNA中并配对相反的规范碱基（A，T，C或G），O 6-甲基鸟嘌呤（O 6 -MeG），O6-苄基鸟嘌呤（O 6 -BnG）或稳定的无碱基位点类似物（四氢呋喃，THF）。根据双链体形成的自由能，当将Peri与O 6- MeG配对时，观察到最高的稳定度。热力学数据表明，较小的探针通过氢键使DNA双链体更稳定，而对π堆栈具有更大容量的较大的探针在碱基堆积的基础上对双链体的稳定做出了更大的贡献。这些结果表明，当BIM，Benzi或Peri与相反的含损伤DNA而不是未修饰的DNA（即O
• OLIGONUCLEOTIDE COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Wave Life Sciences Ltd.

  公开号：EP4022059A1

  公开（公告）日：2022-07-06
• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2021071858A1

  公开（公告）日：2021-04-15

  Among other things, the present disclosure provides oligonucleotides and compositions thereof. In some embodiments, provided oligonucleotides and compositions are useful for adenosine modification. In some embodiments, the present disclosure provides methods for treating various conditions, disorders or diseases that can benefit from adenosine modification.