5'-deoxy-5'-fluoroinosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-deoxy-5'-fluoroinosine
• 英文别名: 5'-fluoro-5'-deoxyinosine；5'-fluoro-5'-deoxinosine；(2S,3S,4R,5R)-2-(Fluoromethyl)-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-3,4-diol；9-[(2R,3R,4S,5S)-5-(fluoromethyl)-3,4-dihydroxyoxolan-2-yl]-1H-purin-6-one
• 化学式: C₁₀H₁₁FN₄O₄
• 分子量: 270.22
• InChiKey: BCNVEAWSQQQYFF-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5'-deoxy-5'-fluoroinosine 在 吡啶 作用下， 反应 1.0h， 以49 mg的产率得到5'-fluoro-5'-deoxy-2',3'-di-O-acetylinosine
  参考文献：
  名称：

  A Facile Synthesis of 5'-Fluoro-5'-deoxyacadesine (5'-F-AICAR): A Novel Non-phosphorylable AICAR Analogue

  摘要：

  用氟原子取代潜在药物中的羟基是一种有效的反应，原则上可以改善药物的药理特性。本文报告了新型化合物 5′-氟-5′-脱氧阿卡地辛（5′-F-AICAR）的合成过程，它是 AICAR 的严格类似物，不能被细胞激酶 5′-磷酸化为 ZMP。

  DOI：

  10.3390/molecules171113036
• 作为产物：
  描述：

  5'-fluoro-5'-deoxyadenosine 在 5'-adenylic acid deaminase from Aspergillus species 作用下， 生成 5'-deoxy-5'-fluoroinosine
  参考文献：
  名称：

  Identification of 5-fluoro-5-deoxy-d-ribose-1-phosphate as an intermediate in fluorometabolite biosynthesis in Streptomyces cattleya

  摘要：

  5'-氟-5'-脱氧-D-核糖-1-磷酸 (FDRP) 被鉴定为卡特兰链霉菌氟代代谢物生物合成过程中的生物合成中间体。

  DOI：

  10.1039/b400754a

文献信息

• Identification of 5-fluoro-5-deoxy-d-ribose-1-phosphate as an intermediate in fluorometabolite biosynthesis in Streptomyces cattleya
  作者：Steven L. Cobb、Hai Deng、John T. G. Hamilton、Ryan P. McGlinchey、David O'Hagan

  DOI：10.1039/b400754a

  日期：——

  5′-Fluoro-5′-deoxy-D-ribose-1-phosphate (FDRP) is identified as a biosynthetic intermediate during fluorometabolite biosynthesis in Streptomyces cattleya.

  5'-氟-5'-脱氧-D-核糖-1-磷酸 (FDRP) 被鉴定为卡特兰链霉菌氟代代谢物生物合成过程中的生物合成中间体。
• Efficient Syntheses of 5‘-Deoxy-5‘-fluoroguanosine and -inosine
  作者：Robert C. Spitale、Moriah G. Heller、Amanda J. Pelly、Joseph E. Wedekind

  DOI：10.1021/jo7015778

  日期：2007.10.1

  medicinal properties of nucleoside analogues. To that end, we present a simple and high-yielding method for the novel synthesis of 5‘-deoxy-5‘-fluoroguanosine and 5‘-deoxy-5‘-fluoroinosine utilizing an intramolecular electron-withdrawing approach. The properties of the resulting modified nucleosides, as well as the halogenated intermediates, are notable for their similarity to nucleoside analogues used in

  用弱氢键受体（如氟）取代氧可提供单原子修饰，这会对核苷类似物的化学和药用特性产生严重影响。为此，我们提出了一种简单且高产的方法，用于利用分子内吸电子方法合成 5'-脱氧-5'-氟鸟苷和 5'-脱氧-5'-氟肌苷。所得修饰核苷以及卤化中间体的特性因其与用于治疗癌症的核苷类似物以及旨在靶向寄生原生动物的酶抑制剂的相似性而显着。
• Cell-Free Biosynthesis of Fluoroacetate and 4-Fluorothreonine in Streptomyces cattleya
  作者：Christoph Schaffrath、Steven L. Cobb、David O'Hagan

  DOI：10.1002/1521-3773(20021018)41:20<3913::aid-anie3913>3.0.co;2-e

  日期：2002.10.18
• The identification of 5′-fluoro-5-deoxyinosine as a shunt product in cell free extracts of Streptomyces cattleya
  作者：Steven L. Cobb、Hai Deng、John T.G. Hamilton、Ryan P. McGlinchey、David O’Hagan、Christoph Schaffrath

  DOI：10.1016/j.bioorg.2005.07.002

  日期：2005.10

  5'-Fluoro-5'-deoxyinosine (5'-FDI) is identified as an adventitious side product that accumulates in cell free incubations of SAM and fluoride ion in Streptomyces cattleya. 5'-FDI was identified by a combination of isotopic labelling studies and co-synthesis studies as well as enzymatic degradation. Although it is an efficiently generated end product of the cell free incubations, 5'-FDI is not a biosynthetic intermediate and it does not accumulate as a fluorometabolite with fluoroacetate and 4-fluorothreonine in whole cell incubations of S. cattleya. Clearly the purine deaminase which converts 5'-fluoro-5'-deoxyadenosine (5'-FDA) to 5'-FDI in the cell free extract does not come into contact with 5'-FDA in whole cells, suggesting some level of compartmentalisation in cells of S. cattleya. The biotransformation of 5'-FDI from fluoride ion extends the range of organofluorine products, beyond biosynthetic intermediates, that can be generated by this system, for applications such as enzymatic labelling with fluorine-18 for positron emission tomography applications. (c) 2005 Elsevier Inc. All rights reserved.
• JPH03133992A
  申请人：——

  公开号：JPH03133992A

  公开（公告）日：1991-06-07