N2,N2,7-trimethylguanosine 5'-monophosphate triethylamine salt | 1325220-77-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: N2,N2,7-trimethylguanosine 5'-monophosphate triethylamine salt
• CAS: 1325220-77-6
• 化学式: C₆H₁₅N*C₁₃H₂₀N₅O₈P
• 分子量: 506.496
• InChiKey: KRKGFGLEPOHMCK-OUTCZKRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.94
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  180.32
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N2,N2,7-trimethylguanosine 5'-monophosphate triethylamine salt 在 2,2'-二硫二吡啶 、 三乙胺 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 triethylammonium N2,N2,7-trimethylguanosine-5'-diphosphate
  参考文献：
  名称：

  合成新型核糖官能化二核苷酸帽类似物，用于帽结合蛋白与mRNA 5'末端相互作用的生物物理研究†

  摘要：

  原始真核生物如的mRNA的秀丽隐杆线虫和蛔虫SUMM具有在其5'末端的两个不同的帽。他们有一个典型的上限，其中包括7-甲基鸟苷通过一个链接5'，5'-三磷酸 桥接至第一个转录的核苷酸（MMG 上限）或在N2位置带有两个额外甲基的非典型超甲基化形式（TMG帽）。mRNA的5'末端与特异性识别其结构的蛋白质之间的相互作用的研究已经进行了数年，并且它们通常需要化学修饰的帽类似物。在这里，我们介绍了五个新的二核苷酸的合成MMG 和 TMG帽类似物，设计用于使用生物物理方法（例如电子自旋共振（ESR）和表面等离子体激元共振（SPR））进行结合研究。新的类似物是通过将2'，3'-顺式二醇 帽结构中第二个核苷酸的 乙酰丙酸，并将获得的缩醛通过其羧基与 4-氨基-2,2,6,6-四甲基哌啶-1-氧基 （4-氨基TEMPO）， 乙二胺 （EDA）或 （+）-生物素-3,6,9-三氧杂十一烷二胺 （胺-PEO

  DOI：

  10.1039/c1ob05425b
• 作为产物：
  描述：

  三乙基碳酸氢铵缓冲液 在 磷酸三甲酯 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 N2,N2,7-trimethylguanosine 5'-monophosphate triethylamine salt
  参考文献：
  名称：

  合成新型核糖官能化二核苷酸帽类似物，用于帽结合蛋白与mRNA 5'末端相互作用的生物物理研究†

  摘要：

  原始真核生物如的mRNA的秀丽隐杆线虫和蛔虫SUMM具有在其5'末端的两个不同的帽。他们有一个典型的上限，其中包括7-甲基鸟苷通过一个链接5'，5'-三磷酸 桥接至第一个转录的核苷酸（MMG 上限）或在N2位置带有两个额外甲基的非典型超甲基化形式（TMG帽）。mRNA的5'末端与特异性识别其结构的蛋白质之间的相互作用的研究已经进行了数年，并且它们通常需要化学修饰的帽类似物。在这里，我们介绍了五个新的二核苷酸的合成MMG 和 TMG帽类似物，设计用于使用生物物理方法（例如电子自旋共振（ESR）和表面等离子体激元共振（SPR））进行结合研究。新的类似物是通过将2'，3'-顺式二醇 帽结构中第二个核苷酸的 乙酰丙酸，并将获得的缩醛通过其羧基与 4-氨基-2,2,6,6-四甲基哌啶-1-氧基 （4-氨基TEMPO）， 乙二胺 （EDA）或 （+）-生物素-3,6,9-三氧杂十一烷二胺 （胺-PEO

  DOI：

  10.1039/c1ob05425b

文献信息

• How to find the optimal partner—studies of snurportin 1 interactions with U snRNA 5′ TMG-cap analogues containing modified 2-amino group of 7-methylguanosine
  作者：Karolina Piecyk、Anna Niedzwiecka、Aleksandra Ferenc-Mrozek、Maciej Lukaszewicz、Edward Darzynkiewicz、Marzena Jankowska-Anyszka

  DOI：10.1016/j.bmc.2015.05.054

  日期：2015.8

  Snurportin 1 is an adaptor protein that mediates the active nuclear import of uridine-rich small nuclear RNAs (U snRNA) by the importin-b receptor pathway. Its cellular activity influences the overall transport yield of small ribonucleoprotein complexes containing N-2,N-2,7-trimethylguanosine (TMG) capped U snRNA. So far little is still known about structural requirements related to molecular recognition of the trimethylguanosine moiety by snurportin in solution. Since these interactions are of a great biomedical importance, we synthesized a series of new 7-methylguanosine cap analogues with extended substituents at the exocyclic 2-amino group to gain a deeper insight into how the TMG-cap is adapted into the snurportin cap-binding pocket. Prepared chemical tools were applied in binding assays using emission spectroscopy. Surprisingly, our results revealed strict selectivity of snurportin towards the TMG-cap structure that relied mainly on its structural stiffness and compactness. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of stability of m3G-CAP analogues in serum-supplemented medium and cytosolic extract
  作者：Malgorzata Honcharenko、Malgorzata Zytek、Burcu Bestas、Pedro Moreno、Jacek Jemielity、Edward Darzynkiewicz、C.I. Edvard Smith、Roger Strömberg

  DOI：10.1016/j.bmc.2013.10.002

  日期：2013.12

  Increased efficiency in splice-correction (splice-switching) has been shown by use of a synthetic RNA 5' end nuclear localization signal composed of an m(3)G-CAP. Use of the m(3)G-CAP as an NLS signal for therapeutic compounds in vivo is likely to require additional stability towards enzymatic degradation. For this reason introduction of stabilizing modifications into the triphosphate bridge may be beneficial. Here we report on synthesis of three m(3)G-CAP derivatives with a 'native' (m(3)GpppA(OMe)) as well as with a methylenephosphonate stabilized triphosphate bridge (m(3)GpCH(2)ppA(OMe), m(3)GppCH(2)pA(OMe)) and the investigation of the enzymatic stability of these compounds in 10% (v/v) fetal bovine serum (FBS) and cytosolic extract from HeLa cells, thus mimicking in vivo conditions. Our results indicate that introduction of methylene group between the beta and gamma phosphates in m(3)GpCH(2)ppAOMe improves to some extent stability of this analogue in 10% serum but does not prolong life of this compound in the cytosolic extract. In contrast the stabilization introduced between alpha and beta phosphates in m(3)GppCH(2)pAOMe offers threefold longer life in 10% serum and almost complete protection in cytosolic extract. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.