5'-fluoro-5'-deoxyadenosine | 731-98-6

• 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'-fluoro-5'-deoxyadenosine
• 英文别名: 5'-FDA；FDA；(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(fluoromethyl)oxolane-3,4-diol
• CAS: 731-98-6
• 化学式: C₁₀H₁₂FN₅O₃
• 分子量: 269.235
• InChiKey: QPVLKMICBYRPSX-KQYNXXCUSA-N

物化性质

• 熔点：
  205-206 °C(Solv: methanol (67-56-1))
• 沸点：
  624.3±65.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：
  119
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，密封保存，干燥环境，避光，惰性气体保护。

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5'-[N-[(3S)-3-amino-3-carboxypropyl]-N,N-dimethylammonium]-5'-deoxyadenosine 在 potassium fluoride 、 L-amino acid oxidase 、 fluorinase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 生成 5'-fluoro-5'-deoxyadenosine
  参考文献：
  名称：

  Enzymatic radiofluorination: Fluorinase accepts methylaza-analog of SAM as substrate for FDA synthesis

  摘要：

  Methylaza-analog of S-adenosyl-L-methionine (MeAzaAdoMet) was found to be a substrate for fluorinase. This is the first discovery of a new substrate for fluorinase that can be accessed synthetically in high purity. The activity of fluorinase for the new MeAzaAdoMet and [F-18]fluoride ion was 32% in 180 min. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.07.015

文献信息

• [EN] NOVEL ANTIBACTERIAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIBACTÉRIENS
  申请人：PASTEUR INSTITUT

  公开号：WO2012090136A1

  公开（公告）日：2012-07-05

  The present invention relates to compounds of formula (I): wherein Rj, R2, R3, R4, Xi, X2, X3 and Z are as defined in claim 1. The compounds are useful in the prevention and/or treatment of bacterial infections.

  本发明涉及以下化合物的公式(I)：其中R1、R2、R3、R4、X1、X2、X3和Z的定义如权利要求1所述。这些化合物在预防和/或治疗细菌感染方面具有用途。
• Novel chemical agents comprising an adenosine moiety or an adenosine analog moiety and an imaging moiety and methods of their use
  申请人：Purohit Ajay

  公开号：US20050106101A1

  公开（公告）日：2005-05-19

  The present invention is directed to novel chemical agents for compounds and their use for imaging myocardial perfusion. The invention also is directed to a kit for forming such novel agents. The chemical agents for the present invention comprising (a) an adenosine analog moiety or an adenosine moiety, and (b) an imaging moiety.

  本发明涉及新型化合物的化学试剂及其用于心肌灌注成像的用途。该发明还涉及用于制备这种新型试剂的试剂盒。本发明的化学试剂包括（a）腺苷类似物基团或腺苷基团，以及（b）成像基团。
• An enzymatic Finkelstein reaction: fluorinase catalyses direct halogen exchange
  作者：Phillip T. Lowe、Steven L. Cobb、David O'Hagan

  DOI：10.1039/c9ob01625b

  日期：——

  respectively to form 5'-fluorodeoxyadenosine (5'-FDA) in the absence of l-methionine (l-Met) or S-adenosyl-l-methionine (SAM). 5'-BrDA is the most efficient substrate for this enzyme catalysed Finkelstein reaction.

  已显示来自牛链霉菌的氟化酶通过5'-溴脱氧腺苷（5'-BrDA）和5'-碘脱氧腺苷（5'-IDA）中的氟离子催化溴和碘的直接置换，形成5'-氟脱氧腺苷（ 5'-FDA），而不含L-甲硫氨酸（L-Met）或S-腺苷-1-甲硫氨酸（SAM）。5'-BrDA是该酶催化的Finkelstein反应的最有效底物。
• Enzymatic fluorination using fluoride ion generated from degradation of fluorinated materials
  作者：Noritaka Iwai、Yuto Tsuboki、Mami Kitazume、Tomoya Kitazume

  DOI：10.1016/j.jfluchem.2009.11.023

  日期：2010.3

  The recycle of fluoride ion generated from the degradation of 1-methyl-3-butylimidazolium tetrafluoroborate, diethyl methyl methoxyethylammonium tetrafluoroborate in the presence of Tris–HCl buffer solution and/or the biodegradation of fluorobenzene and benzotrifluoride, was described. The generated fluoride ion was reused to produce 5′-fluoro-5′-deoxyadenosine (5′-FDA), fluoroacetate and/or 4-fluorothreonine

  描述了在Tris-HCl缓冲溶液的存在下，四氟硼酸1-甲基-3-丁基咪唑鎓四氟硼酸二乙基甲基甲氧基乙基铵的降解和/或氟苯和三氟苯的生物降解产生的氟离子的再循环。产生的氟离子被再利用以产生5'-氟-5'-脱氧腺苷（5'-FDA），氟乙酸盐和/或4-氟苏氨酸。
• An improved synthesis of 5′-fluoro-5′-deoxyadenosines
  作者：Trent D. Ashton、Peter J. Scammells

  DOI：10.1016/j.bmcl.2005.05.029

  日期：2005.7

  Synthesis of 5'-fluoro-5'-deoxyadenosine (5'-FDA) and structurally similar compounds is generally a poor yielding process. This is attributed to the instability of the selected synthetic intermediates. Herein, we report a general synthesis of 5'-fluoro-5'-deoxy-N6-substituted adenosines including a high yielding access to 5'-FDA.

  5'-氟-5'-脱氧腺苷（5'-FDA）和结构相似的化合物的合成通常收率不佳。这归因于所选合成中间体的不稳定性。在本文中，我们报道了5'-氟-5'-脱氧-N6-取代的腺苷的一般合成方法，包括获得5'-FDA的高产率途径。