N⁶-[(2-cyanoethoxy)carbonyl]-2′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)adenosine-3′-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite | 1582753-53-4

• 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: N⁶-[(2-cyanoethoxy)carbonyl]-2′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)adenosine-3′-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS: 1582753-53-4
• 化学式: C₅₀H₆₅N₈O₉PSi
• 分子量: 981.174
• InChiKey: SZZGMDNQDVMWIK-XKEHYBHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.26
• 重原子数：
  69.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  197.36
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 N⁶-[(2-cyanoethoxy)carbonyl]-2′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)adenosine-3′-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Solid-Phase Synthesis and Hybrization Behavior of Partially 2′/3′-O-Acetylated RNA Oligonucleotides

  摘要：

  Synthesis of partially 2'/3'-O-acetylated oligoribonucleotides has been accomplished by using a 2'/3'-O-acetyl orthogonal protecting group strategy in which nonnucleophilic strong-base (DBU) labile nucleobase protecting groups and a LTV-light cleavable linker were used. Strong-base stability of the photolabile linker allowed on-column nucleobase and phosphate deprotection, followed by a mild cleavage of the acetylated oligonucleotides from the solid support with UV light. Two 17nt oligonucleotides, which were synthesized possessing one specific internal 2' or 3'-acetyl group, were used as synthetic standards in a recent report from this laboratory detailing the prebiotically plausible ligation of RNA oligonucleotides. In order to further investigate the effect of 2'/3'-O-acetyl groups on the stability of RNA duplex structure, two complementary bis-acetylated RNA oligonucleotides were also expediently obtained with the newly developed protocols. UV melting curves of 2'-O-acetylated RNA duplexes showed a consistent similar to 3.1 degrees C decrease in T-m per 2'-O-acetyl group.

  DOI：

  10.1021/jo5002824

文献信息

• Site-Specific Synthesis of <i>N</i>⁴-Acetylcytidine in RNA Reveals Physiological Duplex Stabilization
  作者：David Bartee、Kellie D. Nance、Jordan L. Meier

  DOI：10.1021/jacs.1c11985

  日期：2022.3.2

  post-transcriptional modification of RNA that is conserved across all domains of life. All characterized sites of ac4C in eukaryotic RNA occur in the central nucleotide of a 5′-CCG-3′ consensus sequence. However, the thermodynamic consequences of cytidine acetylation in this context have never been assessed due to its challenging synthesis. Here, we report the synthesis and biophysical characterization

  N4-乙酰胞苷 （ac4C） 是 RNA 的转录后修饰，在生命的所有领域中都是保守的。真核 RNA 中 ac4C 的所有特征位点都发生在 5'-CCG-3' 共有序列的中心核苷酸中。然而，由于其具有挑战性的合成，在这种情况下胞苷乙酰化的热力学后果从未被评估过。在这里，我们报道了 ac4C 在其内源性真核序列背景下的合成和生物物理表征。首先，我们开发了一种合成路线，用于含有亲电乙酰基团的均相 RNA。接下来，我们使用热变性来研究 ac4C 对人类 rRNA 中发现的天然序列中双链体稳定性和错配鉴别的生化影响。最后，我们证明了这种化学方法能够将 ac4C 整合到人类 tRNA 的复杂修饰景观中，并使用双链体熔解来强调 ac4C 在这种独特序列背景下的强制作用。通过在生理序列背景下对核酸乙酰化进行离体生物物理分析，这些研究为理解普遍保守的核碱基在生物学和疾病中的功能奠定了化学基础。