(α-D-ribofuranosyl)benzimidazole | 728-02-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 苯并咪唑核糖核苷和核糖核苷酸
• 英文名称: (α-D-ribofuranosyl)benzimidazole
• 英文别名: 1-alpha-d-Ribofuranosylbenzimidazole；(2S,3R,4S,5R)-2-(benzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 728-02-9
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: VQJDOEMQZNKEMJ-KKOKHZNYSA-N

物化性质

• 沸点：
  554.5±60.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(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：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 在 2-fluoro-methylpyridinium tosylate 、 四溴化碳 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (α-D-ribofuranosyl)benzimidazole
  参考文献：
  名称：

  Deprotection of α-imidazole/benzimidazole ribonucleosides by catalytic carbon tetrabromide initiated photolysis

  摘要：

  Several protected benzimidazole and imidazole alpha-ribonucleosides were deprotected in excellent yield Lit ambient temperature using CBr4 initiated photolysis in methanol at ambient temperature. No selectivity was observed and both trityl and isopropylidene groups were deprotected Under the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.180

文献信息

• Recognition of Artificial Nucleobases by<i>E. coli</i>Purine Nucleoside Phosphorylase versus its Ser90Ala Mutant in the Synthesis of Base-Modified Nucleosides
  作者：Ilja V. Fateev、Maria I. Kharitonova、Konstantin V. Antonov、Irina D. Konstantinova、Vasily N. Stepanenko、Roman S. Esipov、Frank Seela、Kartik W. Temburnikar、Katherine L. Seley-Radtke、Vladimir A. Stepchenko、Yuri A. Sokolov、Anatoly I. Miroshnikov、Igor A. Mikhailopulo

  DOI：10.1002/chem.201501334

  日期：2015.9.14

  mechanism of recognition by the wild‐type (WT) E. coli purine nucleoside phosphorylase (PNP) versus its Ser90Ala mutant. The results were analyzed from viewpoint of the role of the Ser90 residue and the structural features of the bases. It was found that the Ser90 residue of the PNP 1) plays an important role in the binding and activation of 8‐aza‐7‐deazapurines in the synthesis of their nucleosides, 2) participates

  广泛的天然嘌呤类似物用作探针，以评估野生型（WT）大肠杆菌嘌呤核苷磷酸化酶（PNP）与其Ser90Ala突变体的识别机制。从Ser90残基的作用和碱基的结构特征的角度分析了结果。发现PNP的Ser90残基在其核苷合成中的8-氮杂-7-脱氮嘌呤的结合和活化中起重要作用; 2）参与α - D-戊呋喃糖-1的结合。在PNP的催化位点处的磷酸，以及3）催化中间形成的2-deoxy-α- D的去磷酸化反式2-脱氧核糖基化反应中的核糖呋喃糖-1-磷酸。5-氮杂-7-脱氮鸟嘌呤对两种酶均表现出优异的底物活性，8-氨基-7-硫杂鸟嘌呤和2-氨基苯并噻唑对两种酶均无底物活性。相反，苯并咪唑和苯并恶唑的2-氨基衍生物是底物，分别被转化为N1-糖苷和不寻常的N2-糖苷。9-Deaza-5-碘黄嘌呤对野生型大肠杆菌PNP具有中等抑制活性，而9-deazaxanthine及其2'-脱氧核糖苷是弱抑制剂。
• Deprotection of α-imidazole/benzimidazole ribonucleosides by catalytic carbon tetrabromide initiated photolysis
  作者：Tilak Chandra、Kenneth L. Brown

  DOI：10.1016/j.tetlet.2005.09.180

  日期：2005.12

  Several protected benzimidazole and imidazole alpha-ribonucleosides were deprotected in excellent yield Lit ambient temperature using CBr4 initiated photolysis in methanol at ambient temperature. No selectivity was observed and both trityl and isopropylidene groups were deprotected Under the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.