2,2-diamino-4-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-5-(2H)-oxazolone | 175980-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-diamino-4-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-5-(2H)-oxazolone
• 英文别名: 2,2-diamino-4-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-2,5-dihydrooxazol-5-one；[(2R,3S,5R)-3-acetyloxy-5-[(2,2-diamino-5-oxo-1,3-oxazolidin-4-ylidene)amino]oxolan-2-yl]methyl acetate
• CAS: 175980-63-9
• 化学式: C₁₂H₁₈N₄O₇
• 分子量: 330.298
• InChiKey: AMLIMTDUGDHTRQ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  165
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-氯苯甲酰乙腈 、 2,2-diamino-4-<(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino>-5-(2H)-oxazolone 反应 0.5h， 生成 Acetic acid (2R,3S)-2-acetoxymethyl-5-methoxyamino-tetrahydro-furan-3-yl ester
  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 、 水 作用下， 以 水 为溶剂， 反应 36.0h， 生成 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：

文献信息

• Reaction of Singlet Oxygen with 2'-Deoxyguanosine and DNA. Isolation and Characterization of the Main Oxidation Products
  作者：Jean-Luc Ravanat、Jean Cadet

  DOI：10.1021/tx00045a009

  日期：1995.4

  The reaction of singlet molecular oxygen with 2'-deoxyguanosine and DNA was studied. Emphasis was placed on the identification and characterization of the main methylene blue mediated type II (singlet oxygen) oxidation products of 2'-deoxyguanosine and its corresponding 3',5'-di-O-acetylated derivative. Two major oxidation products of 2'-deoxyguanosine were isolated and characterized by mass spectrometry

  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
• 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：——