2',3',5'-Tri-O-acetyl-N²-methylguanosine | 4395-48-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3',5'-Tri-O-acetyl-N²-methylguanosine
• 英文别名: 2',3',5'-tri-O-acetyl-2-N-methylguanosine；O^2'_,O3'_,O5'-triacetyl-N²-methyl-guanosine；2',3',5'-Tri-O-acetyl-N²-methylguanosin；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-(methylamino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 4395-48-6
• 化学式: C₁₇H₂₁N₅O₈
• 分子量: 423.382
• InChiKey: DADBIJBLEQQCDX-XNIJJKJLSA-N

物化性质

• 熔点：
  250 °C
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',3',5'-Tri-O-acetyl-N²-methylguanosine 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 反应 0.33h， 以73%的产率得到N2-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
• 作为产物：
  描述：

  2',3',5'-Tri-O-acetyl-N²-(1,3-benzodithiol-2-yl)guanosine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以88%的产率得到2',3',5'-Tri-O-acetyl-N²-methylguanosine
  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

• Synthesis and characterization of modified nucleotides in the 970 hairpin loop of Escherichia coli 16S ribosomal RNA
  作者：N. Dinuka Abeydeera、Christine S. Chow

  DOI：10.1016/j.bmc.2009.07.008

  日期：2009.8

  loop region. Subsequently, stabilities and conformations of the singly and doubly modified RNAs were examined and compared with the corresponding unmodified RNA. Thermodynamic parameters and circular dichroism spectra are presented for the four helix 31 RNA analogues. Surprisingly, methylations in the loop region of helix 31 slightly destabilize the hairpin, which may have subtle effects on ribosome function

  6-合成Ô -DPC -2- Ñ -methylguanosine（米2 G）的核苷和相应的5'- ø 5'-DMT-2'- ø -汤姆保护6- ö -DPC -2- Ñ -methylguanosine据报道，亚磷酰胺 [DPC，二苯基氨基甲酰基；DMT, 4,4'-二甲氧基三苯甲基；TOM，[(三异丙基甲硅烷基)氧基]甲基]。亚磷酰胺的可用性允许通过位点选择性掺入 2- N-甲基鸟苷修饰来合成发夹 RNA 。四个 18-nt 发夹 RNA 类似物，代表大肠杆菌的 970 环区域（螺旋 31 或 h31；U960–A975）合成的 16S rRNA 在环区经过和不经过修饰。随后，检查了单一和双重修饰的 RNA 的稳定性和构象，并与相应的未修饰的 RNA 进行了比较。显示了四种螺旋 31 RNA 类似物的热力学参数和圆二色光谱。令人惊讶的是，螺旋 31 环区域的甲基化会轻微破坏发夹结构，这
• Non-natural peptides as models for the development of antibiotics
  申请人：Cunningham Philip R.

  公开号：US08362203B2

  公开（公告）日：2013-01-29

  Described herein are methods of screening one of the RNA hairpins in the small ribosomal subunit of bacteria to identify peptides that bind to it. The RNA hairpin target may be the 970 loop (aka helix 31 (h31)) or a modified version thereof. The identified peptides may inhibit protein synthesis and, therefore, may be used as a model for new antibiotics.

  本文描述了一种筛选细菌小核糖体亚基中RNA发夹之一以识别与其结合的肽段的方法。RNA发夹的目标可能是970环（也称螺旋31（h31））或其修改版本。已鉴定的肽段可能抑制蛋白质合成，因此可用作新抗生素的模型。
• Non-Natural Peptides as Models for the Development of Antibiotics
  申请人：Cunningham Philip R.

  公开号：US20110021748A1

  公开（公告）日：2011-01-27

  Described herein are methods of screening one of the RNA hairpins in the small ribosomal subunit of bacteria to identify peptides that bind to it. The RNA hairpin target may be the 970 loop (aka helix 31 (h31)) or a modified version thereof. The identified peptides may inhibit protein synthesis and, therefore, may be used as a model for new antibiotics.

  本文介绍了一种筛选细菌小核糖体亚基中RNA发夹之一，以识别与其结合的肽段的方法。RNA发夹的目标可能是970环（也称为31号螺旋（h31））或其修改版本。所识别的肽段可能会抑制蛋白质合成，因此可以用作新型抗生素的模型。
• 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：——