1-(2'-deoxy-5'-O-dimethoxytrityl-β-D-ribofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-pyrimidone | 360048-15-3

• 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: 1-(2'-deoxy-5'-O-dimethoxytrityl-β-D-ribofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-pyrimidone
• CAS: 360048-15-3
• 化学式: C₃₃H₃₃N₅O₆
• 分子量: 595.655
• InChiKey: GWLURYICAONZRM-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  122.75
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(2'-deoxy-5'-O-dimethoxytrityl-β-D-ribofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-pyrimidone 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2'-deoxy-5'-O-dimethoxytrityl-5-methyl-N⁴-oleylcytidine 3'-(N,N-diisopropylamido)-β-cyanoethylphosphite
  参考文献：
  名称：

  摘要：

  A method for directional introduction of oleylamine residues to any position of oligodeoxyribonucleotides during their automated synthesis was developed. The presence of oleylamine residues in 3'- or 5'-terminal nucleotides was shown to have no effect on the thermodynamic stability of DNA duplexes formed by such oligonucleotides and the complementary sequences. The rate of hydrolysis of oligonucleotides containing oleylamine residues in the 3'-terminal units by the snake venom phosphodiesterase was shown to be markedly lower than that of natural oligonucleotides.

  DOI：

  10.1023/a:1011333421540
• 作为产物：
  描述：

  beta-胸苷 在 吡啶 、 三甲基氯硅烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.5h， 生成 1-(2'-deoxy-5'-O-dimethoxytrityl-β-D-ribofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-pyrimidone
  参考文献：
  名称：

  核碱基修饰剂将TET酶鉴定为能够直接进行N-去甲基化的双功能DNA双加氧酶。

  摘要：

  TET家族酶可氧化DNA中5-甲基胞嘧啶（5mC）上的5-甲基取代基。5mC氧化产生稳定的5-羟甲基胞嘧啶碱（5hmC），开始了一个间接的多步骤过程，最终将5mC还原为未修饰的胞嘧啶。在探查5mC识别的核碱基决定因素时，我们发现TET酶也能作为胞嘧啶碱基的直接N-脱甲基酶。我们发现，在缺乏5-甲基的底物上可以很容易地观察到N-脱甲基酶的活性，而且，值得注意的是，TET酶在5mC的氧化或N4-甲基取代基的去甲基化方面具有相似的能力。我们的结果表明，TET酶既可以充当直接脱甲基酶，也可以充当间接脱甲基酶，突出了这些Fe II的活性部位可塑性。/α-酮戊二酸依赖性双加氧酶，并表明在未探索的底物上的活性可能揭示了新的TET生物学。

  DOI：

  10.1002/anie.202002751

文献信息

• WO2008/80060
  申请人：——

  公开号：——

  公开（公告）日：——
• Oxygen Replacement with Selenium at the Thymidine 4-Position for the Se Base Pairing and Crystal Structure Studies
  作者：Jozef Salon、Jia Sheng、Jiansheng Jiang、Guexiong Chen、Julianne Caton-Williams、Zhen Huang

  DOI：10.1021/ja0680919

  日期：2007.4.1

  The T-A and C-G base pairing and stacking allow the formation of the stable DNA duplex structure for genetic information storage, transcription, and replication. To replace the oxygen of the nucleotide nucleobases with selenium for the studies of the base-pair recognition, the duplex stability, and the nuclei acid crystal structures, we have synthesized for the first time the 4-Se thymidine phosphoramidite and incorporated it into oligonucleotides via solid-phase synthesis with high coupling yield (99%). The Se modification on the nucleobase is relatively stable under the elevated temperature. Using the dU(Se) (2'-Se-dU) to facilitate the crystallization, we have successfully crystallized the DNA containing the 4-Se-T substitution and determined its structure at 1.50 A resolution. The UV-melting and X-ray crystal structure studies have indicated that the Se substitution on the nucleobase does not cause a significant structure perturbation, the large Se atom on the thymine can be successfully accommodated by the DNA duplex, and the Se-mediated hydrogen bond (longer than the usual hydrogen bond) is formed within the modified T-A base pair. In addition, the Se derivatization on the nucleobases further facilitates X-ray crystal structure determination of nucleic acids and their protein complexes via Se MAD phasing.