5'-O-(4,4'-dimethoxytrityl)-5-carbomethoxymethyluridine | 321991-67-7

• 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-(4,4'-dimethoxytrityl)-5-carbomethoxymethyluridine
• CAS: 321991-67-7
• 化学式: C₃₃H₃₄N₂O₁₀
• 分子量: 618.64
• InChiKey: VGEYCABFRSDWJH-PYXCEVMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  158.54
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-5-carbomethoxymethyluridine 在 咪唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 3.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-5'-carbomethoxymethyluridine-3'-(cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of tRNA^Lys,3 Anticodon Stem-Loop RNAs Containing the mcm⁵s²U Nucleoside

  摘要：

  Phosphoramidite reagents of the naturally occurring modified nucleosides mcm(5)s(2)U and mcm(5)U were synthesized and along with pseudouridine were incorporated into 17-nucleotide lysine tRNA anticodon stem-loop domains. Standard RNA phosphoramidite coupling chemistry allowed us to systematically investigate the thermodynamic effects of nucleoside modification and to correlate thermodynamic trends with qualitative structure effects seen by NMR spectroscopy.

  DOI：

  10.1021/ol006605h
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 1,2,3,4-四氢-2,4-二氧代-1-beta-D-呋喃核糖基-5-嘧啶乙酸甲酯 在 吡啶 作用下， 以68%的产率得到5'-O-(4,4'-dimethoxytrityl)-5-carbomethoxymethyluridine
  参考文献：
  名称：

  Synthesis and Biophysical Characterization of tRNA^Lys,3 Anticodon Stem-Loop RNAs Containing the mcm⁵s²U Nucleoside

  摘要：

  Phosphoramidite reagents of the naturally occurring modified nucleosides mcm(5)s(2)U and mcm(5)U were synthesized and along with pseudouridine were incorporated into 17-nucleotide lysine tRNA anticodon stem-loop domains. Standard RNA phosphoramidite coupling chemistry allowed us to systematically investigate the thermodynamic effects of nucleoside modification and to correlate thermodynamic trends with qualitative structure effects seen by NMR spectroscopy.

  DOI：

  10.1021/ol006605h

文献信息

• The AlkB Domain of Mammalian ABH8 Catalyzes Hydroxylation of 5-Methoxycarbonylmethyluridine at the Wobble Position of tRNA
  作者：Ye Fu、Qing Dai、Wen Zhang、Jin Ren、Tao Pan、Chuan He

  DOI：10.1002/anie.201001242

  日期：2010.11.15

  Family ties: The AlkB family of nonheme iron, α‐ketoglutarate (αKG)‐dependent dioxygenases is involved in biological processes such as DNA/RNA repair and obesity. The AlkB domain of ABH8 is shown to catalyze the hydroxylation of a modified uridine (mcm5U) into (S)‐mchm5U at the wobble position of the anticodon stem–loop in tRNA (see scheme), thereby suggesting that this protein is a tRNA hypermodification

  家族关系：非血红素铁、α-酮戊二酸 (αKG) 依赖性双加氧酶的 AlkB 家族参与 DNA/RNA 修复和肥胖等生物过程。显示 ABH8 的 AlkB 结构域在 tRNA 中反密码子茎环的摆动位置催化修饰的尿苷 (mcm 5 U)羟基化为 ( S )-mchm 5 U（参见方案），从而表明该蛋白质是一种 tRNA 超修饰酶。