3'-O-methylguanosine 5'-monophosphate triethylammonium salt | 860605-85-2

• 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: 3'-O-methylguanosine 5'-monophosphate triethylammonium salt
• 英文别名: 3'-O-methylguanosine 5'-phosphate triethylammonium salt
• CAS: 860605-85-2
• 化学式: C₆H₁₅N*C₁₁H₁₆N₅O₈P
• 分子量: 478.442
• InChiKey: UVWWKQUSZARYIZ-MCDZGGTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  198.28
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3'-O-methylguanosine 5'-monophosphate triethylammonium salt 在 zinc(II) chloride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 N⁷-(4-chlorophenoxyethyl)-m^3'-OG(5')ppp(5')G triethylammonium salt
  参考文献：
  名称：

  N 7-（4-氯苯氧基乙基）取代的二核苷酸帽类似物用于mRNA翻译的合成及生物学验证

  摘要：

  N 7-（4-氯苯氧基乙基）-G（5'）ppp（5'）G（5a）和N 7-（4-氯苯氧基乙基）-m 3' - O G的二核苷酸帽类似物的设计，合成和生物学验证报告了（5'）ppp（5'）G（5b）。关于N 7-（4-氯苯氧基乙基）取代对盖帽类似物的影响，已经通过使用T7 RNA聚合酶盖帽效率和翻译活性对其体外转录进行了评估。凝胶位移分析表明，新的盖帽类似物（5a，5b）分别显示出77％和76％的盖帽效率，而标准盖帽类似物m 7G（5'）ppp（5'）G的封盖效率为63％。封盖效率实验清楚地表明，N 7修饰的类似物是T7 RNA聚合酶的良好底物。值得注意的是，被N 7-（4-氯苯氧乙基）-m 3'- O G（5'）ppp（5'）G（5b）封端的mRNA poly（A）的翻译效率提高了〜1.64倍，而化合物（5a）的翻译效率是用标准帽类似物加帽的mRNA的〜0.72倍。（5a）观察到的低翻译活

  DOI：

  10.1016/j.bmc.2013.05.041
• 作为产物：
  描述：

  3'-甲氧基鸟苷 、 三乙基碳酸氢铵缓冲液 在 磷酸三乙酯 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 11.0h， 以60%的产率得到3'-O-methylguanosine 5'-monophosphate triethylammonium salt
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR SYNTHESIZING 5'-CAPPED RNAS
  [FR] COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE D'ARN COIFFÉS EN 5'

  摘要：

  本文提供了一种合成5'端帽化RNA的方法和组合物，其中初始帽化寡核苷酸引物的一般形式为m7Gppp[N2'Ome]n[N]m，其中m7G是N7-甲基化鸟苷或任何鸟苷类似物，N是任何天然、修饰或非天然核苷，"n"可以是从0到4的任意整数，"m"可以是从1到9的整数。

  公开号：

  WO2017053297A1

文献信息

• Synthesis and biological evaluation of trimethyl-substituted cap analogs
  作者：Anilkumar R. Kore、Muthian Shanmugasundaram

  DOI：10.1016/j.bmcl.2007.12.049

  日期：2008.2

  The N-7-methyl guanosine cap located on the 5'-terminus of mRNAs is important for a number of biochemical processes. A new dinucleoside triphosphate cap analog was synthesized with methyl groups on the N-7 of both guanine moieties, as well as the (m(2)(7.3'O)G[5']ppp[5']m(7)G). The function of this trimethylated cap analog was compared with those 3'-OH of one of the ribose moieties I of three other, less-methylated cap analogs: one omitting the ribose methylation (m(7)G[5']ppp[5']m(7)G), one omitting the N-7 methylation linked to the unmodified ribose (m(2)(7,3') (O)G[5']ppp[5']G), and the standard cap analog, m(7)G[5']ppp[5']G. These cap modifications were assayed with respect to their effects on capping efficiency, yield of RNAs during in vitro transcription, and the translational activity of these RNAs upon transfection into HeLa cells. The translational activity was monitored by measuring the luciferase activity of a luciferase-fusion protein produced from the in vitro synthesized RNAs. The RNA capped with the trimethylated analog (m(2)(7,3'O)G[5']ppp[5']m(7)G) was translated the most efficiently, with similar to 2.6-fold more activity than the conventional cap (m(7)G[5']ppp[5']G). The other two variants were also more efficient, generating, similar to 2.2 times (for the m(2)(7,3'O)G[5']ppp[5']G analog) and, similar to 1.6 times (for the m(7)G[5']ppp[5']m(7)G analog) more luciferase function than the conventional cap. (C) 2007 Elsevier Ltd. All rights reserved.
• A New Approach to the Synthesis of Anti-Reverse Cap Analog (ARCA) 2mGpppG
  作者：A. L. Kayushin、K. V. Antonov、E. V. Dorofeeva、M. Ya. Berzina、A. O. Arnautova、I. A. Prohorenko、A. I. Miroshnikov、I. D. Konstantinova

  DOI：10.1134/s106816202402033x

  日期：2024.2

  3′-O-methylguanosine only for the synthesis of dimethylated guanosine-5′-monophosphate, and to introduce the activated guanosine-5′-diphosphate into the condensation. Methods: Conditions for phosphorylation of 3′-O-methylguanosine were determined to avoid the formation of by-product 3′-O-methyl-5′-deoxy-5′-chloroguanosine-2′-phosphate. Results and Discussion: At the last step of the synthesis, we used activated