3',5'-di-O-acetyl-8-oxo-7,8-dihydro-2'-deoxyguanosine | 252742-95-3

• 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: 3',5'-di-O-acetyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
• 英文别名: 3',5'-diacetyl-8-oxo-7,8-dihydro-2'-deoxyguanosine；7,8-dihydro-8-oxo-3',5'-di-O-acetyl-2'-guanosine；8-oxo-7,8-dihydro-2'-deoxyguanosine；[(2R,3S,5R)-3-acetyloxy-5-(2-amino-6,8-dioxo-1,7-dihydropurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 252742-95-3
• 化学式: C₁₄H₁₇N₅O₇
• 分子量: 367.318
• InChiKey: RZTFKCBBZUEBOZ-DJLDLDEBSA-N

物化性质

• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-8-oxo-7,8-dihydro-2'-deoxyguanosine 在 CoCl₂ oxone 作用下， 以 phosphate buffer 为溶剂， 反应 0.5h， 生成 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(7-imino-2,4,9-trioxo-1,3,6,8-tetraaza-spiro[4.4]non-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Identification of Products Formed by Reaction of 3‘,5‘-Di-O-acetyl-2‘-deoxyguanosine with Hypochlorous Acid or a Myeloperoxidase−H₂O₂−Cl^- System

  摘要：

  Hypochlorous acid (HOCl), generated by myeloperoxidase from H2O2 and Cl-, plays an important role in host defense and inflammatory tissue injury. We have studied the reaction of 3',5'-di-O-acetyl-2'-deoxyguanosine with reagent HOCl and with a human myeloperoxidase H2O2-Cl- system in order to characterize polar reaction products. When 100 muM 3',5'-di-O-acetyl-2'-deoxyguanosine was reacted with 100 muM HOCl at pH 7.4 and 37 degreesC and the reaction was terminated by N-acetylcysteine, 3',5'-di-O-acetyl derivatives of previously reported products, such as diastereomers of spiroiminodihydantoin nucleoside, a diimino-imidazole nucleoside, an amino-imidazolone nucleoside, and 8-chloro-2'-deoxyguanosine were formed. In addition, we report the formation of 3',5'-di-O-acetyl derivatives of a guanidinohydantoin nucleoside, an iminoallantoin nucleoside, and a diamino-oxazolone nucleoside in this system. The identification of the products was based on their identical ESI-MS and UV spectra and HPLC retention times with authentic compounds synthesized with other oxidation systems. All of these products were also formed in the reaction of 3',5'-di-O-acetyl-2'-deoxyguanosine with the myeloperoxidase-H2O2-Cl- system under mildly acidic conditions. The yields of the products were greatly affected by the pH of the reaction mixture. The total yields of these products formed by HOCl at pH 7.4 and by the myeloperoxidase-H2O2-Cl- system at pH 4.5 were 72 and 43% of the consumed 3',5'-di-O-acetyl-2'-deoxyguanosine, respectively, indicating that nearly half of the consumption of 3',5'-di-O-acetyl-2'-deoxyguanosine by HOCl and the myeloperoxidase-H2O2-Cl- system can be accounted for by the formation of these products.

  DOI：

  10.1021/tx025638y
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 吡啶 、 氧气 、 亚甲兰 作用下， 以 水 为溶剂， 反应 17.0h， 生成 3',5'-di-O-acetyl-8-oxo-7,8-dihydro-2'-deoxyguanosine
  参考文献：
  名称：

  单线态氧与2'-脱氧鸟苷和DNA的反应。主要氧化产物的分离和表征。

  摘要：

  研究了单线态分子氧与2'-脱氧鸟苷和DNA的反应。重点放在鉴定和表征2'-脱氧鸟苷及其相应的3'，5'-di-O-乙酰化衍生物的主要亚甲基蓝介导的II型（单氧）氧化产物上。分离并通过质谱分析和广泛的1H和13C NMR测量分离了2'-脱氧鸟苷的两个主要氧化产物，将其作为4,8-二氢-4-羟基-8-氧代-2'的两个4R *和4S *非对映异构体。 -脱氧鸟苷。还发现在相应的3'，5'-二-O-乙酰化衍生物的碱基部分上出现了1O2的添加。亚甲基蓝介导的2'-脱氧鸟苷的光敏作用还导致产生7,8-二氢-8-oxo-2'-脱氧鸟苷，但相对于上述两种非对映异构体而言，产率相对较低。证实了单线态氧参与这些氧化产物的形成机理。提出了一个合理的机制，该机制涉及通过单线态氧与嘌呤环的Diels-Alder 1,4-环加成反应生成的不稳定内过氧化物的瞬时形成。定量分析使我们能够证明4,8-二氢-4-羟基-8-氧

  DOI：

  10.1021/tx00045a009

文献信息

• Peroxynitrite Reacts with 8-Nitropurines to Yield 8-Oxopurines
  作者：Joseph M. Lee、Jacquin C. Niles、John S. Wishnok、Steven R. Tannenbaum

  DOI：10.1021/tx010093d

  日期：2002.1.1

  the resulting products. Using this model substrate, the products formed during the peroxynitrite reaction were identified as the ethyl derivatives of oxaluric acid, 5-iminoimidazolidin-2,4-dione, III, [N-nitro-N'-[2,4-dioxo-imidazolidine-5-ylidene]-urea, V, dehydroallantoin, parabanic acid, cyanuric acid, and uric acid. Upon the basis of the previous studies with 8-oxodG, these products were recognized

  过氧亚硝酸盐与2'-脱氧鸟苷反应生成几种主要产物，包括8-oxo-2'-脱氧鸟苷（8-oxodG）和8-硝基鸟嘌呤（8-nitroGua）。尽管先前已经表征了在8-oxodG与过氧亚硝酸盐反应过程中形成的末端产物，但没有描述由8-nitroGua形成的末端产物。为了鉴定这些产物，使用9-乙基-8-硝基黄嘌呤作为8-nitroGua的模型，因为前者可以很容易地以高收率合成，并促进了所得产物的反相HPLC分离。使用该模型底物，在过亚硝酸盐反应过程中形成的产物被鉴定为草酸的乙基衍生物，5-亚氨基咪唑烷基-2,4-二酮，III，[N-硝基-N'-[2,4-二氧代-咪唑烷] -5-亚烷基]-脲，V，脱氢丙氨酸，对羟基苯甲酸，氰尿酸和尿酸。根据先前对8-oxodG的研究，这些产品被认为是过氧亚硝酸盐介导的尿酸氧化的产物。此外，反应混合物中尿酸的存在使我们提出了一种模型，其中首先将8-硝基嘌呤转化为8-
• Reaction of 3′,5′-di-O-acetyl-2′-deoxyguansoine with hypobromous acid
  作者：Toshinori Suzuki、Asuka Nakamura、Michiyo Inukai

  DOI：10.1016/j.bmc.2013.04.060

  日期：2013.7

  Hypobromous acid (HOBr) is formed by eosinophil peroxidase and myeloperoxidase in the presence of H2O2, Cl-, and Br- in the host defense system of humans, protecting against invading bacteria. However, the formed HOBr may cause damage to DNA and its components in the host. When a guanine nucleoside (3',5'-di-O-acetyl-2'-deoxyguansoine) was treated with HOBr at pH 7.4, spiroiminodihydantoin, guanidinohydantoin/iminoallantoin, dehydro-iminoallantoin, diimino-imidazole, amino-imidazolone, and diamino-oxazolone nucleosides were generated in addition to an 8-bromoguanine nucleoside. The major products were spiroiminodihydantoin under neutral conditions and guanidinohydantoin/iminoallantoin under mildly acidic conditions. All the products were formed in the reaction with HOCl in the presence of Br-. These products were also produced by eosinophil peroxidase or myeloperoxidase in the presence of H2O2, Cl-, and B-. The results suggest that the products other than 8-bromoguanine may also have importance for mutagenesis by the reaction of HOBr with guanine residues in nucleotides and DNA. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.