3'-O-methylguanosine-5'-monophosphate | 400806-41-9

• 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
• 英文别名: 3'-O-methyl GMP；3'-OMeGMP；5'-Guanylic acid, 3'-O-methyl-；[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-4-hydroxy-3-methoxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 400806-41-9
• 化学式: C₁₁H₁₆N₅O₈P
• 分子量: 377.25
• InChiKey: JGYKGFFURACNNS-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  191
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-O-methylguanosine-5'-monophosphate 在 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  高效合成高度功能化的二核苷酸帽类似物

  摘要：

  的含氨基烯丙基连接子如米新帽类似物的有效合成7 G [5'] PPPP [5'] U形氨基烯丙基和米2 7,3' ö G [5'] PPPP [5'] U形氨基烯丙基报道。在离子交换柱纯化后，最终的帽类似物已经以高纯度（> 99.8％）分离出来。

  DOI：

  10.1016/j.tetlet.2012.04.133
• 作为产物：
  描述：

  3'-甲氧基鸟苷 在 三甲氧基磷 、 三氯氧磷 作用下， 生成 3'-O-methylguanosine-5'-monophosphate
  参考文献：
  名称：

  Synthesis of New Dinucleotide mRNA Cap Analogs Containing 2, 6-Diaminopurine Moiety

  摘要：

  第一个合成具有 2，6-二氨基嘌呤核苷的帽类似物衍生物的实例已被描述。在 ZnCl2 作为催化剂的存在下，2-氨基腺苷[5]单磷酸的咪唑盐与 m7GDP 的相应 TEA 盐发生偶联反应，分别以 73% 和 64% 的收率获得了所需的修饰帽类似物 m7G[5]ppp[5]2-aminoA 6 和 m2 7,3OG[5]ppp[5] 2-aminoA 7。新帽类似物的结构通过 LC/MS、1H 和 31P NMR 得到了证实。

  DOI：

  10.2174/157017810791112388

文献信息

• Synthesis and use of anti-reverse mRBA cap analogues
  申请人：——

  公开号：US20030194759A1

  公开（公告）日：2003-10-16

  The ability to synthesize capped RNA transcripts in vitro has been of considerable value in a variety of applications. However, one-third to one-half of the caps have, until now, been incorporated in the reverse orientation. Such reverse caps impair the translation of in vitro-synthesized mRNAs. Novel cap analogues, such as P 1 -3′-deoxy-7-methylguanosine-5′P 3 -guanosine-5′triphosphate and P 1 -3′-O,7-dimethylguanosine-5′P 3 -guanosine-5′triphosphate, have been designed that are incapable of being incorporated into RNA in the reverse orientation. Transcripts produced with SP6 polymerase using “anti-reverse” cap analogues were of the predicted length. Analysis of the transcripts indicated that reverse caps were not formed. The in vitro translational efficiency of transcripts with the novel “anti-reverse” cap analogues was significantly higher than that of transcripts formed with conventional caps.

  在体外合成带帽RNA转录本的能力在各种应用中具有相当的价值。然而，直到现在，三分之一到一半的帽子都是以反向方向合并的。这种反向帽子会影响体外合成的mRNA的翻译。已经设计出了新的帽子类似物，例如P1-3'-去氧-7-甲基鸟嘌呤-5'P3-鸟嘌呤-5'三磷酸和P1-3'-O，7-二甲基鸟嘌呤-5'P3-鸟嘌呤-5'三磷酸，它们不能以反向方向被合并到RNA中。使用“反向”帽子类似物的SP6聚合酶产生的转录本长度与预期相同。转录本的分析表明没有形成反向帽子。具有新的“反向”帽子类似物的转录本的体外翻译效率显着高于使用传统帽子形成的转录本。
• Synthesis and use of anti-reverse mRNA cap analogues
  申请人：Darzynkiewicz Edward

  公开号：US20060252115A1

  公开（公告）日：2006-11-09

  The ability to synthesize capped RNA transcripts in vitro has been of considerable value in a variety of applications. However, one-third to one-half of the caps have, until now, been incorporated in the reverse orientation. Such reverse caps impair the translation of in vitro-synthesized mRNAs. Novel cap analogues, such as P 1 -3′-deoxy-7-methylguanosine-5′ P 3 -guanosine-5′ triphosphate and P 1 -3′-O,7-dimethylguanosine-5′ P 3 -guanosine-5′ triphosphate, have been designed that are incapable of being incorporated into RNA in the reverse orientation. Transcripts produced with SP6 polymerase using “anti-reverse” cap analogues were of the predicted length. Analysis of the transcripts indicated that reverse caps were not formed. The in vitro translational efficiency of transcripts with the novel “anti-reverse” cap analogues was significantly higher than that of transcripts formed with conventional caps.

  在体外合成带帽RNA转录本的能力在各种应用中具有相当的价值。然而，到目前为止，三分之一到一半的帽子是以反向方向合并的。这些反向帽子会影响体外合成的mRNA的翻译。设计了新的帽子类似物，例如P1-3'-去氧-7-甲基鸟嘌呤-5' P3-鸟嘌呤-5' 三磷酸酯和P1-3'-O，7-二甲基鸟嘌呤-5' P3-鸟嘌呤-5' 三磷酸酯，这些类似物无法以反向方向被合并到RNA中。使用“抗反向”帽子类似物的SP6聚合酶产生的转录本长度与预测长度相同。对转录本的分析表明，没有形成反向帽子。使用新型“抗反向”帽子类似物形成的转录本的体外翻译效率显著高于使用常规帽子形成的转录本。
• Dinucleotide MRNA cap analogs
  申请人：Life Technologies Corporation

  公开号：US08304529B2

  公开（公告）日：2012-11-06

  Novel cap analogs which are easily synthesized, resulting in high levels of capping efficiency and transcription and improved translation efficiencies are provided. Such caps are methylated at the N7 position of one or both guanosines of the dinucleotide cap as well as at the 3′ position on the ribose ring. Substituent groups on the ribose ring also result in the cap being incorporated in the forward orientation. Also provided are methods useful for preparing capped analogs and using mRNA species containing such analogs are also contemplated herein, as well as kits containing the novel cap analogs.

  本发明提供了易于合成的新型帽子类似物，其具有高水平的帽子效率和转录效率以及改善的翻译效率。这些帽子在二核苷酸帽的一个或两个鸟苷的N7位置以及核糖环的3'位置被甲基化。核糖环上的取代基也导致帽子向前定向地被合并。本发明还提供了有用于制备带有这种类似物的mRNA物种的方法，以及包含新型帽子类似物的试剂盒。
• Dinucleotide MRNA CAP Analogs
  申请人：Kore Anilkumar R.

  公开号：US20100261231A1

  公开（公告）日：2010-10-14

  Novel cap analogs which are easily synthesized, resulting in high levels of capping efficiency and transcription and improved translation efficiencies are provided. Such caps are methylated at the N7 position of one or both guanosines of the dinucleotide cap as well as at the 3′ position on the ribose ring. Substituent groups on the ribose ring also result in the cap being incorporated in the forward orientation. Also provided are methods useful for preparing capped analogs and using mRNA species containing such analogs are also contemplated herein, as well as kits containing the novel cap analogs.

  本发明提供了易于合成的小说帽子类似物，导致高水平的帽子效率和转录以及改善的翻译效率。这些帽子在二核苷酸帽的一个或两个鸟嘌呤的N7位置以及核糖环上的3'位置被甲基化。核糖环上的取代基也导致帽子以正向取向被并入。还提供了有用于制备带帽类似物的方法，以及在此考虑了含有这种类似物的mRNA物种的使用，以及含有新型帽子类似物的试剂盒。
• COMPOSITIONS AND METHODS FOR SYNTHESIZING 5 -CAPPED RNAS
  申请人：TriLink BioTechnologies, LLC

  公开号：EP3906789A1

  公开（公告）日：2021-11-10

  Provided herein are methods and compositions for synthesizing 5'Capped RNAs wherein the initiating capped oligonucleotide primers have the general form m7Gppp[N2'Ome]n[N]m wherein m7G is N7-methylated guanosine or any guanosine analog, N is any natural, modified or unnatural nucleoside, "n" can be any integer from 0 to 4 and "m" can be an integer from 1 to 9.

  本文提供了用于合成 5'Capped RNA 的方法和组合物，其中起始的 Capped 寡核苷酸引物具有一般形式 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 0 到 4 之间的任何整数，"m "可以是 1 到 9 之间的整数。