5'-O-(imidolylphospho)-2-N,2-N,7-trimethylguanosine | 178422-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-O-(imidolylphospho)-2-N,2-N,7-trimethylguanosine
• 英文别名: N2,N2,7-trimethylguanosine 5'-monophosphate imidazolide；[(2R,3S,4R,5R)-5-[2-(dimethylamino)-7-methyl-6-oxo-1H-purin-9-ium-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-imidazol-1-ylphosphinate
• CAS: 178422-11-2
• 化学式: C₁₆H₂₂N₇O₇P
• 分子量: 455.367
• InChiKey: IVPBLKIPHYVPSR-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  GTP 、 5'-O-(imidolylphospho)-2-N,2-N,7-trimethylguanosine 在 锰 作用下， 以 水 为溶剂， 生成 m^2,2,73GppppG
  参考文献：
  名称：

  Synthesis and Properties of P1, P2-, P1, P3- and P1, P4-Dinucleoside Di-, Tri- and Tetraphosphate mRNA 5'-Cap Analogues

  摘要：

  DOI：

  10.1080/15257779508012457
• 作为产物：
  描述：

  2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷 在 sodium hydroxide 、 三辛胺 、 2,2'-二硫二吡啶 、 水 、 三乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.33h， 生成 5'-O-(imidolylphospho)-2-N,2-N,7-trimethylguanosine
  参考文献：
  名称：

  Chemical Synthesis of a 5‘-Terminal TMG-Capped Triribonucleotide m₃^2,2,7G^5‘pppAmpUmpA of U1 RNA

  摘要：

  The 5'-terminal TMG-capped triribonucleotide, m(3)(2,2,7)G(5')pppAmpUmpA, has been synthesized by condensation of an appropriately protected triribonucleotide derivative of ppAmpUmpA with a new TMG-capping reagent. During this total synthesis, it was found that the regioselective 2'-O-methylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N-(4-monomethoxytrityl)adenosine was achieved by use of MeI/Ag2O without affecting the base moiety. A new route to 2-N,2-N-dimethylguanosine from guanosine via a three-step reaction has also been developed by reductive methylation using paraformaldehyde and sodium cyanoborohydride. These key intermediates were used as starting materials for the construction of a fully protected derivative of pAmpUmpA and a TMG-capping reagent of Im-pm(3)(2,2,7)G. The target TMG-capped tetramer, m(3)(2,2,7)G(5')pppAmpUmpA, was synthesized by condensation of a partially protected triribonucleotide 5'-terminal diphosphate species, pp(AMMTr)mpUmpA, with Im-pm(3)(2,2,7)G followed by treatment with 80% acetic acid. The structure of m(3)(2,2,7)G(5')pppAmpUmpA was characterized by H-1 and P-31 NMR spectroscopy as well as enzymatic assay using snake venom phosphodiesterase, calf intestinal phosphatase, and nuclease P1.

  DOI：

  10.1021/jo952263v

文献信息

• Clickable trimethylguanosine cap analogs modified within the triphosphate bridge: synthesis, conjugation to RNA and susceptibility to degradation
  作者：Blazej A. Wojtczak、Marcin Warminski、Joanna Kowalska、Maciej Lukaszewicz、Malgorzata Honcharenko、C. I. Edvard Smith、Roger Strömberg、Edward Darzynkiewicz、Jacek Jemielity

  DOI：10.1039/c5ra25684d

  日期：——

  as antisense oligonucleotides. To provide novel tools for studies on m3G-mediated transport and m3G degradation, we synthesized a series of novel m3G cap analogs that combine modifications potentially affecting its activity as an NLS and stability in vivo with a modification enabling simple conjugation to biomolecules. The synthesized dinucleotide m3G analogs carry a single phosphate-modification (phosphorothioate

  存在于小核RNA（snRNA）5'端的三甲基鸟苷（m 3 G）帽已被提出作为针对诸如反义寡核苷酸之类的以核为靶标的治疗剂的有效核定位信号（NLS）。为了提供用于研究m 3 G介导的转运和m 3 G降解的新颖工具，我们合成了一系列新颖的m 3 G帽类似物，这些类似物结合了可能影响其作为NLS活性和体内稳定性的修饰，并具有能够简单偶联的修饰生物分子。合成的二核苷酸m 3G类似物在三磷酸桥的选定位置带有一个磷酸酯修饰基团（硫代磷酸酯，亚甲基双膦酸酯或亚氨基二磷酸酯），以增加其对酶促裂解的抵抗力，并在腺苷的2'-位置带有一个（2-叠氮基乙基）-氨基甲酰基甲基基团。作为第二个核苷酸，可通过铜催化的叠氮化物-炔烃环加成反应（CuAAC）与含炔烃的生物分子偶联。分别在胎牛血清中和在使用hNUDT16酶进行的体外脱盖试验中研究了m 3 G帽类似物对非特异性和特异性降解的敏感性。m 3的磁化率在它们的CuA
• 5′-Terminal chemical capping of spliced leader RNAs
  作者：Karolina Piecyk、Richard E. Davis、Marzena Jankowska-Anyszka

  DOI：10.1016/j.tetlet.2012.06.127

  日期：2012.9

  Spliced leader (SL) RNA trans-splicing adds a N-2,N-2,7-trimethylguanosine cap (TMG) and a 22-nucleotide sequence, the SL, to the 5' end of mRNAs. Both non-trans-spliced with a monomethylguanosine cap (MMG) and trans-spliced mRNAs co-exist in trans-splicing metazoan cells. Efficient translation of TMG-capped mRNAs in nematodes requires a defined core of nucleotides within the SL sequence. Here we present a chemical procedure for the preparation and purification of 5'-terminal capped MMG and TMG wild-type, and mutant 22 nt spliced leader RNAs (GGU/ACUUAAUUACCCAAGUUUGAG) with or without a 3' biotin tag. (C) 2012 Elsevier Ltd. All rights reserved.
• Chemical Synthesis of a 5‘-Terminal TMG-Capped Triribonucleotide m₃^2,2,7G⁵^‘pppAmpUmpA of U1 RNA
  作者：Mitsuo Sekine、Michinori Kadokura、Takahiko Satoh、Kohji Seio、Takeshi Wada、Utz Fischer、Vicki Sumpter、Reinhard Lührmann

  DOI：10.1021/jo952263v

  日期：1996.1.1

  The 5'-terminal TMG-capped triribonucleotide, m(3)(2,2,7)G(5')pppAmpUmpA, has been synthesized by condensation of an appropriately protected triribonucleotide derivative of ppAmpUmpA with a new TMG-capping reagent. During this total synthesis, it was found that the regioselective 2'-O-methylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N-(4-monomethoxytrityl)adenosine was achieved by use of MeI/Ag2O without affecting the base moiety. A new route to 2-N,2-N-dimethylguanosine from guanosine via a three-step reaction has also been developed by reductive methylation using paraformaldehyde and sodium cyanoborohydride. These key intermediates were used as starting materials for the construction of a fully protected derivative of pAmpUmpA and a TMG-capping reagent of Im-pm(3)(2,2,7)G. The target TMG-capped tetramer, m(3)(2,2,7)G(5')pppAmpUmpA, was synthesized by condensation of a partially protected triribonucleotide 5'-terminal diphosphate species, pp(AMMTr)mpUmpA, with Im-pm(3)(2,2,7)G followed by treatment with 80% acetic acid. The structure of m(3)(2,2,7)G(5')pppAmpUmpA was characterized by H-1 and P-31 NMR spectroscopy as well as enzymatic assay using snake venom phosphodiesterase, calf intestinal phosphatase, and nuclease P1.
• Synthesis and Properties of P1, P2-, P1, P3- and P1, P4-Dinucleoside Di-, Tri- and Tetraphosphate mRNA 5'-Cap Analogues
  作者：J. Steogon、pinski、M. Bretner、M. Jankowska、K. Felczak、R. Stolarski、Z. Wieczorek、A-L. Caipostalcode、R. E. Rhoads、A. Temeriusz、D. Haber、E. Darzynkiewicz

  DOI：10.1080/15257779508012457

  日期：1995.5.1