7-methylguanosine 5'-diphosphate | 26467-11-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 7-methylguanosine 5'-diphosphate
• 英文别名: Guanosine 5'-(trihydrogen diphosphate), 7-methyl-, inner salt；[(2R,3S,4R,5R)-5-(2-amino-7-methyl-6-oxo-1H-purin-9-ium-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono phosphate
• CAS: 26467-11-8
• 化学式: C₁₁H₁₇N₅O₁₁P₂
• 分子量: 457.23
• InChiKey: SBASPRRECYVBRF-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  247
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  guanosine 5'-diphosphate disodium salt 、 硫酸二甲酯 在 sodium hydroxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以87%的产率得到7-methylguanosine 5'-diphosphate
  参考文献：
  名称：

  An Industrial Process for Selective Synthesis of 7-methyl Guanosine 5′-Diphosphate: Versatile Synthon for Synthesis of mRNA Cap Analogues

  摘要：

  We report an industrial scale facile synthesis of 7-methyl guanosine 5'-diphosphate, which plays an important role in synthesis of various mRNA cap analogs. An efficient and selective methylation at position 7 of guanosine 5'-diphosphate was achieved by dissolving guanosine 5'-diphosphate in water and drops wise addition of dimethyl sulfate over a period of 1 h at room temperature. The reaction was completed within 2 h and resulted in more than a 96% yield. The desired product, 7-methyl GDP was purified by using BPG column on AKTA Purifier 100. Certainly, this method has advantages over the known methylation method, in terms of yield, economy, safety, and environmental concerns.

  DOI：

  10.1080/15257770500544552

文献信息

• Macrocyclic amines as catalysts of the hydrolysis of the triphosphate bridge of the mRNA 5′-cap structure
  作者：Zhibo Zhang、Harri Lönnberg、Satu Mikkola

  DOI：10.1039/b306268f

  日期：——

  catalysts hydrolysis of the triphosphate bridge predominated. The latter reaction yielded guanosine 5'-monophosphate, guanosine 5'-diphosphate, 7-methylguanosine 5'-monophosphate and 7-methylguanosine 5'-diphosphate as the initial products, indicating that both of the phosphoric anhydride bonds were cleaved. The overall catalytic activity of all three macrocycles was comparable. The hydrolysis to guanosine

  在中性条件下，在三种不同的大环胺（2-4）存在下，研究了5'-帽模型化合物P1-（7-甲基鸟苷）P3-鸟苷5'，5'-三磷酸酯m7GpppG的反应。在不存在大环的情况下观察到的唯一产物是由于碱催化的咪唑开环和N7-甲基鸟苷碱的酸催化裂解，而在这些催化剂的存在下，三磷酸桥的水解作用占主导。后一反应产生鸟苷5′-单磷酸，鸟苷5′-二磷酸，7-甲基鸟苷5′-单磷酸和7-甲基鸟苷5′-二磷酸作为初始产物，表明两个磷酸酐键均被裂解。所有三个大环的总体催化活性是可比的。水解成鸟苷5'-单磷酸和7-甲基鸟苷5'-单磷酸比裂解产生鸟苷5'-单磷酸和7-甲基鸟苷二磷酸稍微更有利。所有大环也增强了随后的核苷二磷酸的水解，其中2比3和4更有效。
• Recognition of different nucleotidyl-derivatives as substrates of reactions catalyzed by various HIT-proteins
  作者：Andrzej Guranowski、Anna Maria Wojdyła、Jarosław Zimny、Anna Wypijewska、Joanna Kowalska、Maciej Łukaszewicz、Jacek Jemielity、Edward Darżynkiewicz、Agata Jagiełło、Paweł Bieganowski

  DOI：10.1039/b9nj00660e

  日期：——

  Proteins that have a histidine triad in their active sites belong to the HIT-protein superfamily. They are ubiquitous, are involved in the metabolism of different nucleotides and catalyze their hydrolysis and/or phosphorolysis liberating either the corresponding 5′-NMP or 5′-NDP, respectively. We studied substrate specificity of nine recombinant HIT-proteins with adenosine 5′-phosphosulfate (1), adenosine 5′-phosphoramidate (2), adenosine 5′-phosphorothioate (3), adenosine 5′-phosphorofluoride (4), diadenosine 5′,5′′′-P1,P3-triphosphate (5), di(7-methylguanosine) 5′,5′′′-P1,P3-triphosphate (6) and adenosine 5′-hypophosphate (7). Preferences for the recognition of these compounds as substrates by individual proteins differed. All the proteins hydrolyzed (1) but the Arabidopsis thaliana Hint1 did it very slowly. None of the proteins cleaved (7). Only A. thaliana Hint1 and Escherichia coli HinT hydrolyzed (3). Three proteins known as dinucleoside triphosphatases, human and A. thaliana Fhit-proteins and Trypanosoma brucei HIT-45, cleaved (1), (2), (4), (5) and (6). Caenorhabditis elegans decapping protein DcpS degraded (1), (5), (6) and poorly (4). A. thaliana aprataxin-like protein and Hint4 hydrolyzed only (1), (2) and (4), in that order of efficiency. Velocities of those reactions and some Km values were determined. Applicability of this study to the metabolism of certain nucleotidyl-derivatives is discussed.

  活性位点具有组氨酸三联体的蛋白质属于 HIT 蛋白质超家族。它们无处不在，参与不同核苷酸的代谢并催化它们的水解和/或磷酸解，分别释放相应的 5'-NMP 或 5'-NDP。我们研究了九种重组 HIT 蛋白的底物特异性，其中包括腺苷 5'-磷酸硫酸酯 (1)、腺苷 5'-氨基磷酸酯 (2)、腺苷 5'-硫代磷酸酯 (3)、腺苷 5'-氟化磷 (4)、二腺苷 5' ,5'''-P1,P3-三磷酸 (5)、二(7-甲基鸟苷) 5',5'''-P1,P3-三磷酸 (6) 和腺苷 5'-连二磷酸 (7)。各个蛋白质对这些化合物作为底物的识别偏好不同。所有蛋白质都会水解 (1)，但拟南芥 Hint1 的水解速度非常缓慢。没有蛋白质被裂解 (7)。仅拟南芥 Hint1 和大肠杆菌 HinT 会水解 (3)。被称为二核苷三磷酸酶、人类和拟南芥 Fhit 蛋白以及布氏锥虫 HIT-45 的三种蛋白质被切割 (1)、(2)、(4)、(5) 和 (6)。秀丽隐杆线虫脱帽蛋白 DcpS 降解 (1)、(5)、(6) 和较差 (4)。拟南芥 aprataxin 样蛋白和 Hint4 按效率顺序仅水解 (1)、(2) 和 (4)。确定了这些反应的速度和一些 Km 值。讨论了本研究对某些核苷酸衍生物代谢的适用性。
• Bojarska, Elzbieta; Stepinski, Janusz; Guranowski, Andrzej, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S192 - S196
  作者：Bojarska, Elzbieta、Stepinski, Janusz、Guranowski, Andrzej、Starzynska, Elzbieta、Chlebicka, Lidia、et al.

  DOI：——

  日期：——
• The Cu²⁺-Promoted Cleavage of mRNA 5′-<i>cap</i>Analogs: A Kinetic Study with P¹-(7-Methylguanosin-5′-yl) P³-(Nucleosid-5′-yl) Triphospates and P¹-(7-Methylguanosin-5′-yl) P⁴-(Guanosin-5′-yl) Tetraphosphate
  作者：Zbigniew Wieczorek、Edward Darzynkiewicz、Satu Kuusela、Harri Lönnberg

  DOI：10.1080/07328319908045590

  日期：1999.1
• An Industrial Process for Selective Synthesis of 7-methyl Guanosine 5′-Diphosphate: Versatile Synthon for Synthesis of mRNA Cap Analogues
  作者：Anilkumar R. Kore、Gaurang Parmar

  DOI：10.1080/15257770500544552

  日期：2006.4.1

  We report an industrial scale facile synthesis of 7-methyl guanosine 5'-diphosphate, which plays an important role in synthesis of various mRNA cap analogs. An efficient and selective methylation at position 7 of guanosine 5'-diphosphate was achieved by dissolving guanosine 5'-diphosphate in water and drops wise addition of dimethyl sulfate over a period of 1 h at room temperature. The reaction was completed within 2 h and resulted in more than a 96% yield. The desired product, 7-methyl GDP was purified by using BPG column on AKTA Purifier 100. Certainly, this method has advantages over the known methylation method, in terms of yield, economy, safety, and environmental concerns.