[(15)N5]guanosine | 204523-20-6

• 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: [(15)N5]guanosine
• 英文别名: 2,1,3,7,9-15N>guanosine；guanosine
• CAS: 204523-20-6
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 288.21
• InChiKey: NYHBQMYGNKIUIF-YYJQJZIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.69
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  159.51
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(15)N5]guanosine 在 焦磷酰氯 、 碳酸氢钠 作用下， 以 aq. buffer 为溶剂， 生成
  参考文献：
  名称：

  Bacterial Pathogen Infection Triggers Magic Spot Nucleotide Signaling in Arabidopsis thaliana Chloroplasts through Specific RelA/SpoT Homologues

  摘要：

  DOI：

  10.1021/jacs.3c04445
• 作为产物：
  描述：

  N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)guanosine 在 ammonium hydroxide 、 sodium methylate 作用下， 生成 [(15)N5]guanosine
  参考文献：
  名称：

  的生物合成生产[ Ñ 2，1,3,7,9- 15 N]鸟苷和[1,3,7,9- 15 N]肌苷和转化成[ Ñ 6，1,3,7,9- 15 Ñ腺苷用于异核NMR鉴定RNA的结构

  摘要：

  通过突变枯草芽孢杆菌菌株的作用，开发了一种生物合成制备15 N标记的鸟苷和肌苷的程序。粗[ Ñ 2，1,3,7,9- 15 N]鸟苷和[1,3,7,9- 15 N]肌苷从通过沉淀和阴离子交换层析（培养滤液中分离方案1）。无需细胞裂解，也无需酶促降解。全异丁酰化衍生物1和2从复杂的混合物中分离纯化产物，通过不同的亲脂性对其进行纯化，然后分三步进行分离，包括正相和反相硅胶色谱法。一升复杂的营养培养基可产生8.44 mmol的鸟苷衍生物和2.84 mmol的肌苷衍生物，平均富集15 N较高（分别为83.5和91.9原子％）。[ Ñ 6，1,3,7,9- 15 N]腺苷（4）从得到的2'，3'，5'-三ö异丁酰基[1,3,7,9- 15 N]肌苷（1）通过将其1,2,4-三唑基衍生物与15 NH 3水溶液氨解（方案2）。

  DOI：

  10.1002/hlca.19950780213

文献信息

• Persistence of N7-(2,3,4-Trihydroxybutyl)guanine Adducts in the Livers of Mice and Rats Exposed to 1,3-Butadiene
  作者：Tomoyuki Oe、Sara J. Kambouris、Vernon E. Walker、Quanxin Meng、Leslie Recio、Suzanne Wherli、Ajai K. Chaudhary、Ian A. Blair

  DOI：10.1021/tx980193s

  日期：1999.3.1

  excess of (+/-)-THBG over meso-THBG in the rat liver at all the time points. In the mouse liver after 10 days of exposure to BD, the (+/-)-THBG (3.9 adducts/10(6) normal bases) was also present in an almost 2-fold excess over meso-THBG (2.2 adducts/10(6) normal bases). However, 6-days after exposure to BD, (+/-)-THBG (1.2 adducts/10(6) normal bases) and meso-THBG (1.0 adduct/10(6) normal bases) were

  液相色谱（LC）与串联质谱（MS / MS）和稳定同位素方法相结合，用于分析由1,2：3、4-二环氧丁烷（BDO2）反应生成的N7-鸟嘌呤（Gua）加合物1,3-丁二烯（BD）的代谢产物。N7-（2,3,4-三羟基丁基）鸟嘌呤（THBG）的两种非对映异构形式在小鼠和大鼠的肝脏中均被鉴定出。非对映异构体之一（（+/-）-THBG）通过DNA与（+/-）-BDO2反应形成，另一个非对映异构体（meso-THBG）通过DNA与meso-BDO2反应形成。与暴露于BD的10天和暴露后6天内的大鼠相比，小鼠的肝脏DNA中有明显更多的（+/-）-THBG和中观THBG。在所有时间点上，大鼠肝脏中的（+/-）-THBG均比中-THBG高出2倍。在暴露于BD的10天后，小鼠肝脏中（+/-）-THBG（3.9加合物/ 10（6）正常碱）的存在量也几乎是中观THBG（2.2加合物/ 10）的2倍（6）正常基础
• Direct Alkylation of Deoxyguanosine by Azaserine Leads to <i>O</i>⁶-Carboxymethyldeoxyguanosine
  作者：Susanne M. Geisen、Claudia M. N. Aloisi、Sabrina M. Huber、Emma S. Sandell、Nora A. Escher、Shana J. Sturla

  DOI：10.1021/acs.chemrestox.0c00471

  日期：2021.6.21

  The O6-alkylguanosine adduct O6-carboxymethyldeoxyguanosine (O6-CMdG) has been detected at elevated levels in blood and tissue samples from colorectal cancer patients and from healthy volunteers after consuming red meat. The diazo compound l-azaserine leads to the formation of O6-CMdG as well as the corresponding methyl adduct O6-methyldeoxyguanosine (O6-MedG) in cells and is therefore in wide use

  所述Ô 6 -alkylguanosine加合物ø 6 -carboxymethyldeoxyguanosine（ø 6 -CMdG）已经在结肠直肠癌患者的血液和组织样品中升高的水平和来自健康志愿者的消耗红肉后检测。重氮化合物l-氮杂丝氨酸导致O 6 -CMdG 以及相应的甲基加合物O 6 -甲基脱氧鸟苷 ( O 6 -MedG) 在细胞中的形成，因此在有关 DNA 损伤的细胞研究中被广泛用作化学探针和突变。然而，关于l形成 DNA 加合物的化学基础仍然存在知识空白。- 氮芥。为了表征l -氮杂丝氨酸形成的O 6 -CMdG ，我们进行了化学和酶稳定性和反应性研究的组合，该研究由液相色谱串联质谱法支持，用于同时定量O 6 -CMdG 和O 6 -MedG。我们发现l-氮杂丝氨酸在生理和碱性条件下以及在活性生物基质中都是稳定的，但会发生酸催化水解。我们首次表明l-氮杂丝氨酸直接与鸟苷 (dG)
• Characterization of a Lipid Hydroperoxide-Derived RNA Adduct in Rat Intestinal Epithelial Cells
  作者：Peijuan Zhu、Seon Hwa Lee、Suzanne Wehrli、Ian A. Blair

  DOI：10.1021/tx0600189

  日期：2006.6.1

  Five major products (adducts A(1a), A(1b), A(2), A(3), and B) from the reaction of guanosine (Guo) with 4-oxo-2(E)-nonenal (ONE) were detected by liquid chromatography-mass spectrometry (LC-MS). Tandem MS (MS/MS) analysis of these compounds suggested that modifications to the nucleoside had been introduced. Adducts A1a, A1b, A2, and A3 were heptanone-ethano-2'-Guo adducts that all decomposed to adduct B. Adducts A1a and A1b were isomeric hemi-ketal forms. Adducts A2 and A3 were diastereomers of the open chain ketone form. The structure of adduct B was shown by LC-MS/MS and NMR spectroscopy to be the heptanone-etheno-Guo (H epsilon Guo) adduct, 3-(D-erythropentafuranosyl)imidazo-7(heptane-2"-one)-9-hydroxyl[1,2-alpha] purine. The overall reaction of Guo with ONE was very similar to its reaction with 2'-deoxyguanosine. Reaction of ONE with yeast transfer RNA also resulted in the formation of H epsilon Guo. Finally, H epsilon Guo was detected and quantified in the RNA from rat intestinal epithelial cells that stably express cyclooxygenase-2. These data show that RNA is modified by the same bifunctional reactive electrophiles derived from lipid peroxidation that covalently modify DNA.