2'-deoxy-β-D-ribosyl urea | 33501-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-deoxy-β-D-ribosyl urea
• 英文别名: (2-Deoxy-beta-D-erythro-pentofuranosyl)urea；[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]urea
• CAS: 33501-14-3
• 化学式: C₆H₁₂N₂O₄
• 分子量: 176.172
• InChiKey: QPADYGQDEFABBT-VPENINKCSA-N

物化性质

• 沸点：
  419.3±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-deoxy-β-D-ribosyl urea 、 5-溴水杨醛 在 Montmorillonite K-10 clay 、 ammonium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.13h， 以72%的产率得到4-Amino-6-bromo-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3,4-dihydro-benzo[e][1,3]oxazin-2-one
  参考文献：
  名称：

  Three-component coupling strategy for the expeditious synthesis of novel 4-aminobenzoxazinone N-nucleosides

  摘要：

  One-pot montmorillonite K-10 clay-supported three-component reactions Of Substituted salicylaldehydes, ribosyl/deoxyribosylureas and ammonium acetate expeditiously yield the novel N-nucleosides, 4-amino-3,4-dihydro-3-(beta-D-ribo- or beta-D-2'-deoxyribofuranosyl)-2H-benz[e]-1,3-oxazin-2-ones, via cycloisomerisation of an aldimine intermediate under solvent-free microwave irradiation conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.006
• 作为产物：
  描述：

  glycol de thymidine 在 alkalin hydrolysis at pH 10 作用下， 以 水 为溶剂， 生成 2'-deoxy-β-D-ribosyl urea 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Boorstein, R. J.; Cadet, J.; Hilbert, T., Journal de Chimie Physique et de Physico-Chimie Biologique, 1993, vol. 90, # 4, p. 837 - 852

  摘要：

  DOI：

文献信息

• The reactions of thymine and thymidine with ozone
  作者：Roman Flyunt、Jacob A. Theruvathu、Achim Leitzke、Clemens von Sonntag

  DOI：10.1039/b204067k

  日期：2002.8.27

  The ozonolysis of thymine and thymidine has been investigated by a product study complemented by kinetic studies using spectrophotometry, conductometry and stopped-flow with optical and conductometric detection. Material balance has been obtained. Ozonolysis of thymine (k = 3.4 × 104 dm3 mol−1 s−1) leads to the formation of the acidic (pKa = 4) hydroperoxide 1-hydroperoxymethylene-3-(2-oxopropanoyl)urea 5 (∼34%), neutral hydroperoxides (possibly mainly 1-hydroperoxyhydroxymethyl-3-(2-oxopropanoyl)urea 6, total ∼41%) and H2O2 (25%, with corresponding formation of 1-formyl-5-hydroxy-5-methylhydantoin 11). The organic hydroperoxides decay (∼1.1 × 10−3 s−1 at 20 °C, 1.3 × 10−4 s−1 at 3 °C) releasing formic acid (formation of 5-hydroperoxy-5-methylhydantoin 18) and also to some extent H2O2 (and 11). After 100 min, the formic acid yield is 75%. Upon treatment at high pH, it increases to 100%. Reduction of the organic hydroperoxides with bis(2-hydroxyethyl) sulfide (k = 50 dm3 mol−1 s−1) leads to 11 whose subsequent treatment with base yields 5-hydroxy-5-methylhydantoin 13 in 100% yield. It is suggested that the Criegee ozonide formed upon reaction with ozone at the C(5)–C(6) double bond opens heterolytically in two directions with subsequent opening of the C(5)–C(6) bond. In the preferred route (75%), the positive charge resides at C(6). Deprotonation at N(1) gives rise to 5, while its reaction with water yields 6. Loss of formic acid yields 5-hydroperoxy-5-methylhydantoin 18. Reduction of 5 and 6 with the sulfide yields 11. In the minor route (25%), the positive charge remains at C(5) followed by a reaction with water. The resulting α-hydroxy hydroperoxide rapidly loses H2O2 (formation of 11). In basic solution, singlet dioxygen is formed (8%). The concomitant product, 5,6-dihydroxy-5,6-dihydrothymine has been detected. In the ozonolysis of thymidine, the rapid formation of conductance (k = 0.55 s−1) is due to the release of acetic acid (18%). In this reaction a short-lived hydroperoxide is destroyed. As a consequence of this, 25 s after ozonolysis the total hydroperoxide yield is only ∼78% (including 8% H2O2). The products corresponding to acetic acid are suggested to be CO2 and N-(2-deoxy-β-D-erythropentofuranosyl)formylurea 22. A number of organic hydroperoxides have been detected by HPLC by post-column derivatisation with iodide. An acidic hydroperoxide such as 5 in the case of thymine is not among the products. Upon sulfide reduction, the organic hydroperoxides yield mainly (43–50%) N1-(2-deoxy-β-D-erythropentofuranosyl)-5-hydroxy-5-methylhydantoin 23. The reasons for some striking differences in the ozonolyses of thymine and thymidine are discussed.

  胸腺嘧啶和胸腺嘧啶脱氧核苷的臭氧化反应已通过产物研究和利用分光光度法、电导法和带有光学和电导检测的停流技术的动力学研究得到补充。得到了物料平衡。胸腺嘧啶（k= 3.4 × 104 dm3 mol−1 s−1）的臭氧化反应导致形成酸性（pKa= 4）氢过氧化物1-羟过氧亚甲基-3-（2-氧丙酰基）脲5（约34%）、中性氢过氧化物（可能主要是1-羟过氧羟甲基-3-（2-氧丙酰基）脲6，总计约41%）和H2O2（25%，相应地形成1-甲酰基-5-羟基-5-甲基乙内酰脲11）。有机氢过氧化物衰减（20 °C下约为1.1 × 10−3 s−1，3 °C下为1.3 × 10−4 s−1），释放甲酸（形成5-羟过氧-5-甲基乙内酰脲18），也在一定程度上释放 （和11）。100分钟后，甲酸产率为75%。在碱性高pH条件下处理后，产率增加到100%。用二（2-羟乙基）硫醚（k= 50 dm3 mol−1 s−1）还原有机氢过氧化物，产生11，其后续在碱性条件下的处理以100%的产率得到5-羟基-5-甲基乙内酰脲13。提出的机理是，在C(5)-C(6)双键与臭氧反应形成的Criegee臭氧化物在两个方向上异裂开环，随后C(5)-C(6)键断裂。在优先的路径（75%）中，正电荷位于C(6)。在N(1)处去质子化产生5，而其与水的反应产生6。失去甲酸形成5-羟过氧-5-甲基乙内酰脲18。用硫醚还原5和6产生11。在次要路径（25%）中，正电荷保持在C(5)，然后与水反应。产生的α-羟基氢过氧化物迅速失去 （形成11）。在碱性溶液中，形成单线态双氧（8%）。同时产物5,6-二羟基-5,6-二氢胸腺嘧啶已被检测到。在胸腺嘧啶脱氧核苷的臭氧化反应中，快速形成的电导（k= 0.55 s−1）是由于释放乙酸（18%）。在这个反应中，一种短寿命的氢过氧化物被破坏。因此，臭氧化反应25秒后，总氢过氧化物产率仅为约78%（包括8% ）。与乙酸对应的产物被认为是CO2和N-(2-脱氧-β-D-赤藓糖戊糖基)甲酰脲22。通过碘化物的柱后衍生化，通过HPLC检测到多种有机氢过氧化物。像胸腺嘧啶中的5这样的酸性氢过氧化物不在产物之列。用硫醚还原时，有机氢过氧化物主要（43-50%）产生的为N1-(2-脱氧-β-D-赤藓糖戊糖基)-5-羟基-5-甲基乙内酰脲23。讨论了胸腺嘧啶和胸腺嘧啶脱氧核苷臭氧化反应中一些显著差异的原因。
• Investigations of electron-transfer reactions and the redox mechanism of 2′-deoxyguanosine-5′-monophosphate using electrochemical techniques
  作者：Rajendra N. Goyal、Sham M. Sondhi、Anand M. Lahoti

  DOI：10.1039/b415452p

  日期：——

  Electron-transfer reactions of 2′-deoxyguanosine-5′-monophosphate (dGMP) have been investigated in phosphate buffers of different pH at a pyrolytic graphite electrode (PGE). In cyclic voltammetry, two well-defined oxidation peaks, Ia (pH 1.9–10.6) and IIa (pH ≥ 5.8), were noticed. The peak potentials shifted towards less positive potential when pH was increased. Concentration and sweep rate studies established the adsorption of dGMP on the electrode surface. UV-vis spectral analysis at pH 2.9 and 7.1 indicated formation of a UV-absorbing intermediate, which decayed in a pseudo first-order reaction (k = ∼5.05 × 10−4 s−1). Coulometric, voltammetric and UV studies revealed the 4H+,4e− oxidation of dGMP by an EC (electrode reactions followed by chemical reactions) mechanism. The characterization of the oxidation products was achieved by converting them to their trimethylsilyl derivatives. At pH 7.1, 5-hydroxyhydantoin-5-carboxamide (9) and a N–O–C8 linked trimer (18) and, at pH 2.9, monohydrated alloxan (12), deoxyriboside urea (11), two C8O–OC8 and one C8–C8 bridged dimers of dGMP (13, 14 and 15, respectively) were formed as the major oxidation products. A tentative redox mechanism has been suggested for the electrooxidation of dGMP.

  已在热解石墨电极 (PGE) 的不同 pH 磷酸盐缓冲液中研究了 2-脱氧鸟苷-5-单磷酸 (dGMP) 的电子转移反应。在循环伏安法中，注意到两个明确的氧化峰，Ia (pH 1.9-10.6) 和 IIa (pH ≤ 5.8)。当 pH 值增加时，峰值电势向较小的正电势移动。浓度和扫描速率研究确定了 dGMP 在电极表面上的吸附。 pH 2.9 和 7.1 下的紫外可见光谱分析表明形成了紫外吸收中间体，该中间体在伪一级反应中衰变 (k = 5.05 10 4 s 1)。库仑分析、伏安分析和紫外研究揭示了 dGMP 的 4H+,4e-氧化是通过 EC（电极反应随后发生化学反应）机制实现的。氧化产物的表征是通过将其转化为三甲基甲硅烷基衍生物来实现的。 pH 7.1 时，5-羟基乙内酰脲-5-甲酰胺 (9) 和 N-O-C8 连接三聚体 (18)，pH 2.9 时，一水合四氧嘧啶 (12)、脱氧核苷脲 (11)、两个 C8O- OC8 和 dGMP 的一个 C8→C8 桥接二聚体（分别为 13、14 和 15）作为主要氧化产物形成。已经提出了一种用于 dGMP 电氧化的尝试性氧化还原机制。
• Insights into the Biological Redox Chemistry of 2′-Deoxyadenosine 5′-Monophosphate by Electrochemical Techniques
  作者：Rajendra N. Goyal、Aikta Dhawan

  DOI：10.1246/bcsj.78.1944

  日期：2005.11

  The electrochemical oxidation of 2′-deoxyadenosine 5′-monophosphate at a pyrolytic graphite electrode (PGE) was studied in the pH range 2.65–10.03 and was found to proceed in a single well-defined ...

  在 2.65-10.03 的 pH 值范围内研究了 2'-脱氧腺苷 5'-单磷酸酯在热解石墨电极 (PGE) 上的电化学氧化，并发现在单个明确定义的...
• Mechanism of degradation of 2′-deoxycytidine by formamide: Implications for chemical DNA sequencing procedures
  作者：Raffaele Saladino、Claudia Crestini、Enrico Mincione、Giovanna Costanzo、Ernesto Di Mauro、Rodolfo Negri

  DOI：10.1016/s0968-0896(97)00140-5

  日期：1997.11

  We describe the reaction of formamide with 2'-deoxycytidine to give pyrimidine ring opening by nucleophilic addition on the electrophilic C(6) and C(4) positions. This information is confirmed by the analysis of the products of formamide attack on 2'-deoxycytidine, 5-methyl-2'-deoxycytidine, and 5-bromo-2'-deoxycytidine, residues when the latter are incorporated into oligonucleotides by DNA polymerase-driven

  我们描述了甲酰胺与2'-脱氧胞苷的反应，通过亲电C（6）和C（4）位置上的亲核加成得到嘧啶开环。该信息通过分析甲酰胺对2'-脱氧胞苷，5-甲基-2'-脱氧胞苷和5-溴-2'-脱氧胞苷的残基的攻击分析得到证实，这些残基通过DNA聚合酶-驱动聚合和固相亚磷酰胺程序。相对于2'-脱氧胞苷，5-溴-2'-脱氧胞苷的敏感性提高对于基于甲酰胺与DNA的碱基选择性反应改进单泳道DNA测序过程至关重要。实际上，在许多DNA测序的情况下，可以将这种碱基类似物掺入要测序的DNA中，因此，可以完全区分其紫外线吸收信号和胸苷残基的紫外线吸收信号。2'-脱氧胞苷类似物显示出的对甲酰胺的多种不同敏感性，在DNA单泳道化学测序程序中解决了由于C和T残基之间的低区分度而导致的错误来源。
• Antimicrobial compounds, compositions, and uses thereof
  申请人：Lakewood Amedex, Inc.

  公开号：US10752651B2

  公开（公告）日：2020-08-25

  Antimicrobial compounds and compositions of Formula (I) and methods of use are disclosed.

  本发明公开了式（I）的抗菌化合物和组合物以及使用方法。