8-oxoinosine | 63699-77-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-oxoinosine
• 英文别名: 8-oxo-7,8-dihydroinosine；9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-hydroxy-7H-purin-8(9H)-one；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
• CAS: 63699-77-4
• 化学式: C₁₀H₁₂N₄O₆
• 分子量: 284.228
• InChiKey: ZQIXICISNQZUQJ-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  20
• 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：
  144
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-oxoinosine 在 吡啶 、 氯化亚砜 作用下， 反应 48.0h， 生成 6-chloro-8-oxo-7,8-dihydropururinoriboside tribenzoate
  参考文献：
  名称：

  Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy

  摘要：

  Oxidative damage to purine nucleic acid bases proceeds through quinoidal intermediates derived from their corresponding 8-oxo-7,8-dihydropurine bases. Oxidation studies of 8-oxo-7,8-dihyroadenosine and 8-oxo-7,8-dihydroinosine indicate that these quinoidal species can produce stable cross links with a wide variety of nucleophiles in the 2-positions of the purines. An azide precursor for the adenosine iminoquinone has been synthesized and applied in ultrafast transient absorption spectroscopic studies. Thus, the adenosine iminoquinone can be observed directly, and its susceptibility to nudeophilic attack with various nucleophiles as well as the stability of the resulting cross linked species have been evaluated Finally, these observations indicate that this azide might be a very useful photoaffurity labeling agent, because the reactive intermediate, adenosine iminoquinone, is such a good mimic for the universal purine base adenosine.

  DOI：

  10.1021/ja3068148
• 作为产物：
  描述：

  8-氧腺苷 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以50%的产率得到8-oxoinosine
  参考文献：
  名称：

  Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy

  摘要：

  Oxidative damage to purine nucleic acid bases proceeds through quinoidal intermediates derived from their corresponding 8-oxo-7,8-dihydropurine bases. Oxidation studies of 8-oxo-7,8-dihyroadenosine and 8-oxo-7,8-dihydroinosine indicate that these quinoidal species can produce stable cross links with a wide variety of nucleophiles in the 2-positions of the purines. An azide precursor for the adenosine iminoquinone has been synthesized and applied in ultrafast transient absorption spectroscopic studies. Thus, the adenosine iminoquinone can be observed directly, and its susceptibility to nudeophilic attack with various nucleophiles as well as the stability of the resulting cross linked species have been evaluated Finally, these observations indicate that this azide might be a very useful photoaffurity labeling agent, because the reactive intermediate, adenosine iminoquinone, is such a good mimic for the universal purine base adenosine.

  DOI：

  10.1021/ja3068148

文献信息

• The Supramolecular Helical Architecture of 8-Oxoinosine and 8-Oxoguanosine Derivatives
  作者：Stefano Lena、Mauro A. Cremonini、Francesco Federiconi、Giovanni Gottarelli、Carla Graziano、Luca Laghi、Paolo Mariani、Stefano Masiero、Silvia Pieraccini、Gian Piero Spada

  DOI：10.1002/chem.200601126

  日期：2007.4.16

  The 8-oxoguanosine derivative 1 and the 8-oxoinosine derivative 2 b, with appropriate substituents on their ribose moieties, form hexagonal lyotropic mesophases in hydrocarbon solvents. Small-angle X-ray scattering analysis of a film of 1 and of the mesophase of 2 b, and NMR and CD spectra of isotropic solutions of 2 b, indicate that in both cases the supramolecular structures adopted are continuous

  在其核糖部分上具有适当取代基的8-氧代鸟苷衍生物1和8-氧代肌苷衍生物2b在烃溶剂中形成六方溶致中间相。薄膜1和中间相2 b的小角X射线散射分析以及2 b的各向同性溶液的NMR和CD光谱表明，在两种情况下，采用的超分子结构都是由氢原子形成的连续螺旋。杂环碱基之间的键网络。值得注意的是，虽然在其核糖部分上带有大取代基的衍生物2b经历自组装和中间相形成，但是在核糖部分上仅具有癸酰基的氧代肌苷2a却没有。这可能归因于后者的两亲性能降低和没有芳族基团。
• [DE] VERFAHREN UND NUCLEINSÄUREVERBINDUNG ZUM ABBAU VON IN-VITRO SYNTHETISIERTEN NUCLEINSÄUREMOLEKÜLEN<br/>[EN] METHOD AND NUCLEIC ACID COMPOUND FOR BREAKING DOWN NUCLEIC ACID MOLECULES SYNTHESIZED IN VITRO<br/>[FR] PROCEDE ET COMPOSE D'ACIDE NUCLEIQUE POUR LA DECOMPOSITION DE MOLECULES D'ACIDE NUCLEIQUE SYNTHETISEES IN VITRO
  申请人：MIRA DIAGNOSTIKA GMBH

  公开号：WO1999050447A1

  公开（公告）日：1999-10-07

  (DE) Verfahren zum Abbau von Nucleinsäuremolekülen, wobei in einem abzubauenden Nucleinsäuremolekül Nucleoside des abzubauenden Nucleinsäuremoleküls durch eine chemische Modifikationsreaktion in Nucleosidanaloga umgewandelt werden, die von Nucleinsäure-Glycosylasen als deren Substrat erkannt werden; Zugabe der Nucleinsäure-Glycosylase zu einer Probe, in der das abzubauende Nucleinsäuremolekül vorhanden ist und die abzubauende Nucleinsäure durch Reaktion der zugegebenen Nucleinsäure-Glycosylase abgebaut wird. Des weiteren werden Nucleinsäureverbindungen offenbart, bei denen in der Polymerkette mindestens eine Struktureinheit vorgesehen ist, die mindestens eine Erkennungsstelle für Nucleasen, Glycosylasen, und/oder Methylasen und mindestens eine transformierbare Gruppe aufweist, die nach einer Transformation die Erkennungsstelle freilegt.(EN) The invention relates to a method for breaking down nucleic acid molecules, comprising the following steps: in a nucleic acid molecule to be broken down nucleosides of said nucleic acid molecule are converted by a chemical modification reaction into nucleoside analogues which are recognized by nucleic acid glycosylases as their substrate; the nucleic acid glycosylase is added to a sample containing the nucleic acid molecule to be broken down; and the nucleic acid to be broken down is broken down by reaction with the added nucleic acid glycosylase. The invention also relates to nucleic acid compounds which in the polymer chain have at least one structural unit having at least one recognition site for nucleases, glycosylases and/or methylases and at least one transformable group which frees the recognition site after a transformation.(FR) L'invention concerne un procédé pour la décomposition de molécules d'acide nucléique qui comporte les étapes suivantes: transformation dans une molécule d'acide nucléique à décomposer, par une réaction de modification chimique, de nucléosides de la molécule d'acide nucléique à décomposer en analogues de nucléoside reconnus par des glycosylases d'acide nucléique comme leur substrat, adjonction de la glycosylase d'acide nucléique à un échantillon contenant la molécule d'acide nucléique à décomposer et, enfin, décomposition de l'acide nucléique à décomposer par réaction de la glycosylase d'acide nucléique ajoutée. L'invention concerne également des composés d'acide nucléique comprenant, dans la chaîne polymérique, au moins une unité structurale qui présente au moins un site de reconnaissance pour nucléases, glycosylases ou méthylases et au moins un groupe transformable qui dégage le site de reconnaissance après une transformation.

  一种核酸分子分解的方法，其特征在于：将一种核酸分子（即被分解的核酸分子）中的核酸苷经化学修饰反应转化为核酸苷相类物质（即被识别为特定核酸糖苷酶底物的核酸苷相类物质），将其添加到包含被分解的核酸分子的试样中，并使该被分解的核酸分子与此种核酸糖苷酶发生反应而降解；该方法还涉及一种核酸化合物，这样的核酸化合物包含于其聚合链中的至少一个结构单元，该结构单元至少具有一个核酸酶、核酸糖苷酶或甲基化酶的识别部位以及至少一个可转换基团，这样的可转换基团在线性转换处理后使该识别部位自生成。
• Autoxidation of pentaammineruthenium(III)-nucleoside complexes: xanthine oxidase activity in a simple compound without oxo-atom transfer
  作者：K. C. Gariepy、M. A. Curtin、Michael J. Clarke

  DOI：10.1021/ja00195a058

  日期：1989.6
• MASSIVELY PARALLEL ENZYMATIC SYNTHESIS OF NUCLEIC ACID STRANDS
  申请人：DNA Script

  公开号：EP3826762A1

  公开（公告）日：2021-06-02
• ONE POT SYNTHESIS OF SETS OF OLIGONUCLEOTIDES
  申请人：DNA Script

  公开号：EP3906317A1

  公开（公告）日：2021-11-10