5'-O-dimethoxytrityl-(2'S)-2'-deoxy-2'-C-methyluridine | 402518-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-dimethoxytrityl-(2'S)-2'-deoxy-2'-C-methyluridine
• 英文别名: 1-[(2R,3S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-methyloxolan-2-yl]pyrimidine-2,4-dione
• CAS: 402518-18-7
• 化学式: C₃₁H₃₂N₂O₇
• 分子量: 544.604
• InChiKey: GRRFZFXOLWJVGM-AQFJBESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5'-O-dimethoxytrityl-(2'S)-2'-deoxy-2'-C-methyluridine 在 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以73%的产率得到5'-O-dimethoxytrityl-(2'S)-2'-deoxy-2'-C-methyluridine-3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  合成与性能（2'小号） -和（2' - [R）-2'-脱氧-2'- Ç甲基寡核苷酸

  摘要：

  的合成（2'小号） -和（2' - [R）-2'-脱氧-2'- Ç甲基Ñ 3 - （4-吨-butylbenzoyl）尿苷，（2'小号）-2'-脱氧-2'- ç -methyluridine和（2'小号）-2'-脱氧-2'- ç甲基ñ 4异丁酰基胞苷积木在这里描述。提出了在所有位置但3'-端均携带这些单体的寡核苷酸的制备方法，并评估了这些新片段与互补DNA和RNA序列之间的结合亲和力。（2′R）取代的寡核苷酸既不与互补的DNA序列又不与RNA序列杂交。然而，含有（2 'S）修饰的寡核苷酸的杂交体的解链曲线的一阶导数表示解链转变。

  DOI：

  10.1016/s0040-4020(01)00745-1
• 作为产物：
  描述：

  1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 在 四丁基氟化铵 、 氢气 、 对甲苯磺酰氯 、 四甲基胍 、 2-硝基苯甲醛肟 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 12.0h， 生成 5'-O-dimethoxytrityl-(2'S)-2'-deoxy-2'-C-methyluridine
  参考文献：
  名称：

  Influence of conformationally restricted pyrimidines on the activity of 10–23 DNAzymes

  摘要：

  The catalytic core of a 10-23 DNAzyme was modified introducing conformationally restricted nucleosides such as (2'R)-, (2'S)-2'-deoxy-2'-C-methyluridine, (2'R)-, (2'S)-2'-deoxy-2'-C-methylcytidine, 2,2'-anhydrouridine and LNA-C, in one, two or three positions. Catalytic activities under pseudo first order conditions were compared at different Mg2+ concentrations using a short RNA substrate. At low Mg2+ concentrations, triple modified DNAzymes with similar kinetic performance to that displayed by the non-modified control were identified. In the search for a partial explanation of the obtained results, in silico studies were carried out in order to explore the conformational behavior of 2'-deoxy-2'-C-methyl-pyrimidines in the context of a loop structure, suggesting that at least partial flexibility is needed for the maintenance of activity. Finally, the modified 2'-C-methyl DNAzyme activity was tested assessing the inhibition of Stat3 expression and the decrease in cell proliferation using the human breast cancer cell line T47D. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.047

文献信息

• Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides
  作者：Daniel O Cicero、Mariana Gallo、Philippe J Neuner、Adolfo M Iribarren

  DOI：10.1016/s0040-4020(01)00745-1

  日期：2001.9

  The synthesis of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl-N3-(4-t-butylbenzoyl) uridine, (2′S)-2′-deoxy-2′-C-methyluridine and (2′S)-2′-deoxy-2′-C-methyl-N4-isobutyryl cytidine building blocks are here described. The preparation of oligonucleotides carrying these monomers in all positions but 3′-end is presented and the binding affinity between these new fragments and the complementary DNA and RNA sequences

  的合成（2'小号） -和（2' - [R）-2'-脱氧-2'- Ç甲基Ñ 3 - （4-吨-butylbenzoyl）尿苷，（2'小号）-2'-脱氧-2'- ç -methyluridine和（2'小号）-2'-脱氧-2'- ç甲基ñ 4异丁酰基胞苷积木在这里描述。提出了在所有位置但3'-端均携带这些单体的寡核苷酸的制备方法，并评估了这些新片段与互补DNA和RNA序列之间的结合亲和力。（2′R）取代的寡核苷酸既不与互补的DNA序列又不与RNA序列杂交。然而，含有（2 'S）修饰的寡核苷酸的杂交体的解链曲线的一阶导数表示解链转变。
• Influence of conformationally restricted pyrimidines on the activity of 10–23 DNAzymes
  作者：Laura Robaldo、Franco Izzo、María Dellafiore、Cecilia Proietti、Patricia V. Elizalde、Javier M. Montserrat、Adolfo M. Iribarren

  DOI：10.1016/j.bmc.2012.02.047

  日期：2012.4

  The catalytic core of a 10-23 DNAzyme was modified introducing conformationally restricted nucleosides such as (2'R)-, (2'S)-2'-deoxy-2'-C-methyluridine, (2'R)-, (2'S)-2'-deoxy-2'-C-methylcytidine, 2,2'-anhydrouridine and LNA-C, in one, two or three positions. Catalytic activities under pseudo first order conditions were compared at different Mg2+ concentrations using a short RNA substrate. At low Mg2+ concentrations, triple modified DNAzymes with similar kinetic performance to that displayed by the non-modified control were identified. In the search for a partial explanation of the obtained results, in silico studies were carried out in order to explore the conformational behavior of 2'-deoxy-2'-C-methyl-pyrimidines in the context of a loop structure, suggesting that at least partial flexibility is needed for the maintenance of activity. Finally, the modified 2'-C-methyl DNAzyme activity was tested assessing the inhibition of Stat3 expression and the decrease in cell proliferation using the human breast cancer cell line T47D. (C) 2012 Elsevier Ltd. All rights reserved.