2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷 | 73196-87-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷
• 英文名称: 2′,3′,5′-tri-O-acetyl-N²,N²-dimethylguanosine
• 英文别名: 2',3',5'-Tri-O-acetyl-N²,N²-dimethylguanosine；2',3',5'-tri-O-acetyl-2-N,2-N-dimethylguanosine；2',3',5'-Tri-O-acetyl-2N,2N-dimethyl Guanosine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-(dimethylamino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 73196-87-9
• 化学式: C₁₈H₂₃N₅O₈
• 分子量: 437.409
• InChiKey: GZKPCWCCXJQIPH-LSCFUAHRSA-N

物化性质

• 熔点：
  113-119°C
• 密度：
  1.54±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷 在 吡啶 、 磷酸三甲酯 、 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 生成 N⁷,N²,N²-trimethylguanosine 5'-methylenepyrophosphate tris(triethylamine)salt
  参考文献：
  名称：

  Complex and method for enhancing nuclear delivery

  摘要：

  使用至少一个基于核定位信号的核酸，包括天然或合成的m3G-CAP，已经显示出增加分子载体，特别是大分子，进入细胞核的跨膜转运。使用天然和合成的m3G-CAP已被披露，并且通过一个示例展示了天然RNA 5'端核定位信号，由一个2,2,7-三甲基鸟苷CAP（m3G-CAP）与荧光链霉素结合，在另一个示例中则是与一个反义寡核苷酸结合。一种甲基磷酸酯修饰的m3G-CAP已经显示出在人类血清和细胞质提取物中具有改善的稳定性。

  公开号：

  US09067964B2
• 作为产物：
  描述：

  2',3',5'-Tri-O-acetyl-N²-methyl-N²-<(p-tolylthio)methyl>guanosine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以95%的产率得到2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷
  参考文献：
  名称：

  A convenient method for the synthesis of N2,N2-dimethylguanosine by reductive carbon-sulfur bond cleavage with tributyltin hydride

  摘要：

  A new method for the N-methylation of guanosine is described. The 1,3-benzodithiol-2-yl group was introduced into the 2-amino group of 2',3',5'-tri-O-acetylguanosine (3) and then converted into a methyl group by reductive C-S bond cleavage with tributyltin hydride. This method was also applied to the synthesis of N2,N2-dimethylguanosine. A similar reductive conversion of a (p-tolylthio)methyl group into a methyl group was studied.

  DOI：

  10.1021/jo00003a052

文献信息

• COMPLEX AND METHOD FOR ENHANCING NUCLEAR DELIVERY
  申请人：Smith Edvard

  公开号：US20110306138A1

  公开（公告）日：2011-12-15

  The use of at least one nucleic acid based nuclear localization signal including a natural or synthetic m 3 G-CAP is shown to increase transmembrane transport of a molecular cargo, in particular large molecules, into the nucleus. The use of natural and synthetic m 3 G-CAP is disclosed and the effect shown with a natural RNA 5′ end nuclear localization signal composed of a 2,2,7-trimethylguanosine CAP (m 3 G-CAP) coupled to fluorescent Streptavidin in one example, and an antisense oligonucleotide in another. A methylenephosphonate modified m 3 G-CAP is shown to have improved stability in human serum and in cytosolic extract.

  本发明展示了至少使用一个基于核酸的核定位信号，其中包括自然或合成的m3G-CAP，可增加分子货物的跨膜转运，尤其是大分子，进入细胞核。本发明揭示了自然和合成的m3G-CAP的使用，并且在一个示例中显示了一种由2,2,7-三甲基鸟嘌呤CAP（m3G-CAP）组成的自然RNA 5'末端核定位信号与荧光链霉亲和素偶联，以及在另一个示例中使用反义寡核苷酸。显示了甲基磷酸酯修饰的m3G-CAP在人血清和胞质提取物中具有改善的稳定性。
• 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.
• SEKINE, MITSUO;SATOH, TAKAHIKO, J. ORG. CHEM., 56,(1991) N, C. 1224-1227
  作者：SEKINE, MITSUO、SATOH, TAKAHIKO

  DOI：——

  日期：——
• US9067964B2
  申请人：——

  公开号：US9067964B2

  公开（公告）日：2015-06-30
• A convenient method for the synthesis of N2,N2-dimethylguanosine by reductive carbon-sulfur bond cleavage with tributyltin hydride
  作者：Mitsuo Sekine、Takahiko Satoh

  DOI：10.1021/jo00003a052

  日期：1991.2

  A new method for the N-methylation of guanosine is described. The 1,3-benzodithiol-2-yl group was introduced into the 2-amino group of 2',3',5'-tri-O-acetylguanosine (3) and then converted into a methyl group by reductive C-S bond cleavage with tributyltin hydride. This method was also applied to the synthesis of N2,N2-dimethylguanosine. A similar reductive conversion of a (p-tolylthio)methyl group into a methyl group was studied.