2-amino-5-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-4H-imidazol-4-one | 175980-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-amino-5-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-4H-imidazol-4-one
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-[(2-amino-5-oxo-1H-imidazol-4-ylidene)amino]oxolan-2-yl]methyl acetate
• CAS: 175980-62-8
• 化学式: C₁₂H₁₆N₄O₆
• 分子量: 312.282
• InChiKey: PKLVFPOLXMTURQ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-5-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-4H-imidazol-4-one 在 水 作用下， 反应 24.0h， 以31.8 mg的产率得到2,2-diamino-4-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-5-(2H)-oxazolone
  参考文献：
  名称：

  Raoul, Sebastien; Berger, Maurice; Buchko, Garry W., Journal of the Chemical Society. Perkin transactions II, 1996, # 3, p. 371 - 382

  摘要：

  DOI：
• 作为产物：
  描述：

  3',5'-di-O-acetyl-2'-deoxyguanosine 在 二苯甲酮 作用下， 以 水 为溶剂， 反应 12.0h， 以13%的产率得到2-amino-5-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-4H-imidazol-4-one
  参考文献：
  名称：

  Raoul, Sebastien; Berger, Maurice; Buchko, Garry W., Journal of the Chemical Society. Perkin transactions II, 1996, # 3, p. 371 - 382

  摘要：

  DOI：

文献信息

• Discovery and Mutagenicity of a Guanidinoformimine Lesion as a new Intermediate of the Oxidative Deoxyguanosine Degradation Pathway
  作者：Dimitrios Stathis、Ulrike Lischke、Sandra C. Koch、Christian A. Deiml、Thomas Carell

  DOI：10.1021/ja211435d

  日期：2012.3.14

  Oxidative degradation of DNA is a major mutagenic process. Reactive oxygen species (ROS) produced in the course of oxidative phosphorylation or by exogenous factors are known to attack preferentially deoxyguanosine. The latter decomposes to give mutagenic lesions, which under physiological conditions are efficiently repaired by specialized maintenance systems in the cell. Although many intermediates of the degradation pathway are today well-known, we report in this study the discovery of a new intermediate with an interesting guanidinoformimine structure. The structure elucidation of the new lesion was possible by using HPLC-MS techniques and organic synthesis. Finally we report the mutagenic potential of the new lesion in comparison to the known lesions imidazolone and oxazolone using primer extension and pyrosequencing experiments.
• 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.
• Identification of Products Formed by Reaction of 3‘,5‘-Di-<i>O</i>-acetyl-2‘-deoxyguanosine with Hypochlorous Acid or a Myeloperoxidase−H₂O₂−Cl^- System
  作者：Toshinori Suzuki、Marlin D. Friesen、Hiroshi Ohshima

  DOI：10.1021/tx025638y

  日期：2003.3.1

  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.
• Cadet; Berger; Buchko, Journal of the American Chemical Society, 1994, vol. 116, # 16, p. 7403 - 7404
  作者：Cadet、Berger、Buchko、Joshi、Raoul、Ravanat

  DOI：——

  日期：——