2-N,2-N,7-trimethylguanosine 5'-O-phosphate | 29885-97-0

• 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: 2-N,2-N,7-trimethylguanosine 5'-O-phosphate
• 英文别名: N²-Dimethyl-N⁷-methylguanosin-5'-phosphorsaeure；N(2),N(2),N(7)-trimethylguanosine 5'-phosphate；[(2R,3S,4R,5R)-5-[2-(dimethylamino)-7-methyl-6-oxo-1H-purin-9-ium-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 29885-97-0
• 化学式: C₁₃H₂₀N₅O₈P
• 分子量: 405.304
• InChiKey: ZKNRLOCMOKOKHW-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-N,2-N,7-trimethylguanosine 5'-O-phosphate 生成 [(3aR,4R,6R,6aS)-4-[2-(dimethylamino)-7-methyl-6-oxo-1H-purin-9-ium-9-yl]-2-phenyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaborol-6-yl]methoxy-imidazol-1-ylphosphinate 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Solid-phase synthesis of a 5′-terminal TMG-capped trinucleotide block of U1 snRNA

  摘要：

  A 5'-terminal 2,2,7-trimethylguanosine-capped trinucleotide block (m(3)(2,2,7)G(5')pppAmpUmpA) was successfully synthesized on a highly cross-linked polystyrene resin by a new method for introduction of the first nucleoside onto the resin and a newly developed pyrophosphorylating agent having a benzotriazolyloxy substitutent as the leaving group. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01941-4
• 作为产物：
  描述：

  2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷 在 sodium hydroxide 、 水 、 三氯氧磷 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.33h， 生成 2-N,2-N,7-trimethylguanosine 5'-O-phosphate
  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

• 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.
• Solid-phase synthesis of a 5′-terminal TMG-capped trinucleotide block of U1 snRNA
  作者：Michinori Kadokura、Takeshi Wada、Kohji Seio、Tomohisa Moriguchi、Jochen Huber、Reinhard Lührmann、Mitsuo Sekine

  DOI：10.1016/s0040-4039(01)01941-4

  日期：2001.12

  A 5'-terminal 2,2,7-trimethylguanosine-capped trinucleotide block (m(3)(2,2,7)G(5')pppAmpUmpA) was successfully synthesized on a highly cross-linked polystyrene resin by a new method for introduction of the first nucleoside onto the resin and a newly developed pyrophosphorylating agent having a benzotriazolyloxy substitutent as the leaving group. (C) 2001 Published by Elsevier Science Ltd.