2',3'-O-isopropylidene-5-aminomethyluridine | 89129-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2',3'-O-isopropylidene-5-aminomethyluridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(aminomethyl)pyrimidine-2,4-dione
• CAS: 89129-13-5
• 化学式: C₁₃H₁₉N₃O₆
• 分子量: 313.31
• InChiKey: UKLAJFLMNNOBES-TURQNECASA-N

物化性质

• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-5-aminomethyluridine 在 吡啶 、 四氮唑 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 氨苯砜 作用下， 反应 1.5h， 生成
  参考文献：
  名称：

  Sekine; Seio; Wada, Journal of the American Chemical Society, 1994, vol. 116, # 10, p. 4469 - 4470

  摘要：

  DOI：
• 作为产物：
  描述：

  1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-piperidin-1-ylmethyl-1H-pyrimidine-2,4-dione 在 ammonium hydroxide 、 三苯基膦 作用下， 反应 6.0h， 生成 2',3'-O-isopropylidene-5-aminomethyluridine
  参考文献：
  名称：

  Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif

  摘要：

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.

  DOI：

  10.1021/jo971797o

文献信息

• The modified nucleosides from the “ wobble position ” of tRNAs. The synthesis of 5-carboxymethylaminomethyluridine and 5-carboxymethylaminomethyl-2-thiouridine
  作者：A. Małkiewicz、E. Sochacka、A.F. Sayed Ahmed、S. Yassin

  DOI：10.1016/s0040-4039(00)87878-8

  日期：——

  The synthesis of 5-carboxymethylaminomethyluridine isolated from tRNA1Gly (B. subtilis) and its 2-thio analogue from tRNALys (B. subtilis) have been described.

  已经描述了从tRNA 1 Gly（枯草芽孢杆菌）分离的5-羧甲基氨基甲基尿苷及其从tRNA Lys（枯草芽孢杆菌）的2-硫类似物的合成。