m₂^7,3'OG[5']ppp[5']G | 400806-46-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: m₂^7,3'OG[5']ppp[5']G
• 英文别名: [[(2R,3S,4R,5R)-5-(2-amino-7-methyl-6-oxo-1H-purin-9-ium-9-yl)-4-hydroxy-3-methoxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphate
• CAS: 400806-46-4
• 化学式: C₂₂H₃₁N₁₀O₁₈P₃
• 分子量: 816.466
• InChiKey: AIRSQUYUYJSIIM-XPWFQUROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.3
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  402
• 氢给体数：
  9
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  、 鸟苷 5'-磷酰咪唑 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以70%的产率得到m₂^7,3'OG[5']ppp[5']G
  参考文献：
  名称：

  Synthesis and biological evaluation of trimethyl-substituted cap analogs

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.12.049

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.