2-amino-4-oxo-5-formamido-6-pyrimidine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-4-oxo-5-formamido-6-pyrimidine
• 英文别名: 2,6-diamino-4-hydroxy-5-formamidopyrimidine nucleoside；N-(2-Amino-4-(((2'R,5'R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)amino)-6-oxo-1,6-dihydropyrimidin-5-yl)formamide)；N-[2-amino-4-[[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]amino]-6-oxo-1H-pyrimidin-5-yl]formamide
• 化学式: C₁₀H₁₅N₅O₅
• 分子量: 285.26
• InChiKey: ZQARXNLMOXVNBE-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2-双-(4-甘胺氧苯)丙烷 、 2-amino-4-oxo-5-formamido-6-pyrimidine 以 甲醇 、 丙酮 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Thermospray liquid chromatography-mass spectrometry of the DNA adducts formed between 2′-deoxynucleosides and bisphenol A diglycidyl ether

  摘要：

  通过高效液相色谱法（HPLC）和热喷雾液相色谱-质谱法分析了2'-脱氧腺苷（dAdo）、2'-脱氧胞苷（dCyd）、2'-脱氧尿苷（dUrd）、2'-脱氧鸟苷（dGuo）与双酚A二缩水甘油醚（BPADGE）形成的加合物。开发了一种使用5RP8选B柱（125 × 4 mm内径）和甲醇/0.1 M NH4OAc流动相（流速为0.8 ml min^-1）的HPLC方法。通过固相萃取开发了一种样品富集程序，并发现其富集因子平均值为9。单加合物通过强烈的[BH + H]+、[BH + Na]+和[S]+离子信号进行表征。观察到BPADGE/dGuo加合物中咪唑环开环，表明烷基化发生在N-7位。由于观察到水解脱氨反应导致BPADGE/dUrd加合物形成，将BPADGE/dCyd加合物中的烷基化位点归属于N-3。未观察到交联现象。

  DOI：

  10.1002/jms.1190301011
• 作为产物：
  描述：

  2'-脱氧鸟苷 、 formamide 生成 2,4-二氨基-5-甲酰氨基-6-羟基嘧啶 、 2-amino-4-oxo-5-formamido-6-pyrimidine
  参考文献：
  名称：

  Mechanism of Degradation of Purine Nucleosides by Formamide. Implications for Chemical DNA Sequencing Procedures

  摘要：

  We describe the reaction of formamide with 2'-deoxyadenosine and 2'-deoxyguanosine to give imidazole ring opening by nucleophilic addition on the electrophilic C(8)-position of the purine ring. This information allows improvement of the one-lane chemical DNA sequencing procedure based on the base-selective reaction of formamide with DNA. The reactivity with formamide of several 7-deazapurine analogues (7-deaza-2'-deoxyinosine, 7-deaza-2'-deoxyguanosine, and 7-deaza-2'-deoxyadenosine) incorporated into polynucleotides is also described. The wide spectrum of different sensitivities to formamide displayed by these purine analogues provides the single-lane DNA chemical sequencing procedures with the possibility of wide-ranging signal intensity modulation and thus increased specificity.

  DOI：

  10.1021/ja953527y

文献信息

• Hydroxyl radical-induced degradation of 2′-deoxyguanosine under reducing conditions
  作者：Thierry Douki、Sandrine Spinelli、Jean-Luc Ravanat、Jean Cadet

  DOI：10.1039/a903690c

  日期：——

  Addition of hydroxyl radical to the base moiety of 2′-deoxyguanosine (dGuo) leads to the formation of two main radicals exhibiting oxidising and reducing properties, respectively. The oxidising radical reacts with oxygen to yield 2,2-diamino-5-[2-deoxy-β-D-erythro-pentofuranosyl)amino]oxazol-5(2H)-one (oxazolone) as the final product. The reducing radical is either preferentially oxidised into 8-oxo-7

  将羟基自由基加到2'-脱氧鸟苷（dGuo）的碱基部分上导致形成分别表现出氧化和还原性质的两个主要自由基。氧化性自由基与氧反应生成2,2-二氨基-5- [2-脱氧-β - D-赤型-戊呋喃糖基）氨基]恶唑-5（2 H）-（恶唑酮）为最终产物。还原基团可以优先氧化成8-oxo-7,8-dihydro-2'-deoxyguanosine（8-oxodGuo）或还原成2,6-二氨基-4-羟基-5-甲酰胺基嘧啶衍生物（FapydGuo），具体取决于情况。我们在这里报告说，还原化合物（抗坏血酸或半胱氨酸）的存在强烈地修饰了dGuo充气水溶液的γ辐射后修饰核苷的分布。恶唑酮的收率下降，而8-oxodGuo和FapydGuo的收率上升。这可以通过氧化自由基的还原来解释，该氧化自由基通过氧化和还原嘌呤自由基之间的反应阻止了dGuo的还原。该研究扩展到了N光化学释放˙OH时dGuo的分解-羟基嘧啶-2-硫酮（
• Thermospray liquid chromatography-mass spectrometry of the DNA adducts formed between 2′-deoxynucleosides and bisphenol A diglycidyl ether
  作者：K. Vanhoutte、P. Joos、F. Lemière、W. Van Dongen、E. L. Esmans、M. Claeys、E. Van den Eeckhout

  DOI：10.1002/jms.1190301011

  日期：1995.10

  The adducts formed between 2′-deoxyadenosine (dAdo), 2′-deoxycytidine (dCyd), 2′-deoxycytidine (dUrd), 2′-deoxyguanosine (dGuo) and bisphenol A diglycidyl ether (BPADGE) were analysed by high-performance liquid chromatography (HPLC) and thermospray liquid chromatography–mass spectrometry. An HPLC method was developed using a 5RP8 select B column (125 × 4 mm i.d.) and a mobile phase of MeOH/0.1 M NH4OAc at a flow-rate of 0.8 ml min−1. A sample enrichment procedure using solid phase extraction was developed and was found to result in an enrichment factor with a mean value of 9. Mono-adducts were characterized by intense [BH + H]+, [BH + Na]+ and [S]+ ion signals. Imidazole ring opening was observed for the BPADGE/dGuo adduct indicating that the alkylation occurs at N-7. The alkylation site in the BPADGE/dCyd adduct was assigned to N-3 because a hydrolytic deamination reaction was observed leading to the BPADGE/dUrd adduct. Crosslinking was not observed.

  通过高效液相色谱法（HPLC）和热喷雾液相色谱-质谱法分析了2'-脱氧腺苷（dAdo）、2'-脱氧胞苷（dCyd）、2'-脱氧尿苷（dUrd）、2'-脱氧鸟苷（dGuo）与双酚A二缩水甘油醚（BPADGE）形成的加合物。开发了一种使用5RP8选B柱（125 × 4 mm内径）和甲醇/0.1 M NH4OAc流动相（流速为0.8 ml min^-1）的HPLC方法。通过固相萃取开发了一种样品富集程序，并发现其富集因子平均值为9。单加合物通过强烈的[BH + H]+、[BH + Na]+和[S]+离子信号进行表征。观察到BPADGE/dGuo加合物中咪唑环开环，表明烷基化发生在N-7位。由于观察到水解脱氨反应导致BPADGE/dUrd加合物形成，将BPADGE/dCyd加合物中的烷基化位点归属于N-3。未观察到交联现象。
• Mechanism of Degradation of Purine Nucleosides by Formamide. Implications for Chemical DNA Sequencing Procedures
  作者：Raffaele Saladino、Enrico Mincione、Claudia Crestini、Rodolfo Negri、Ernesto Di Mauro、Giovanna Costanzo

  DOI：10.1021/ja953527y

  日期：1996.1.1

  We describe the reaction of formamide with 2'-deoxyadenosine and 2'-deoxyguanosine to give imidazole ring opening by nucleophilic addition on the electrophilic C(8)-position of the purine ring. This information allows improvement of the one-lane chemical DNA sequencing procedure based on the base-selective reaction of formamide with DNA. The reactivity with formamide of several 7-deazapurine analogues (7-deaza-2'-deoxyinosine, 7-deaza-2'-deoxyguanosine, and 7-deaza-2'-deoxyadenosine) incorporated into polynucleotides is also described. The wide spectrum of different sensitivities to formamide displayed by these purine analogues provides the single-lane DNA chemical sequencing procedures with the possibility of wide-ranging signal intensity modulation and thus increased specificity.