2',3'-di-O-acetyluridine-5'-carboxylic acid | 148116-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3'-di-O-acetyluridine-5'-carboxylic acid
• 英文别名: (2S,3S,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolane-2-carboxylic acid
• CAS: 148116-17-0
• 化学式: C₁₃H₁₄N₂O₉
• 分子量: 342.262
• InChiKey: OTDHYMNNJXBIJT-ZRUFSTJUSA-N

物化性质

• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.62
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  153.99
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-acetyluridine-5'-carboxylic acid 在 硫化氢 、 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 、 水 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding

  摘要：

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.002
• 作为产物：
  描述：

  2',3'-di-O-acetyl-5'-(triphenylmethyl)uridine 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 2',3'-di-O-acetyluridine-5'-carboxylic acid
  参考文献：
  名称：

  Timoshchuk, V. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 7, p. 1198 - 1204

  摘要：

  DOI：

文献信息

• Design of Glycosyltransferase Inhibitors: Serine Analogues as Pyrophosphate Surrogates?
  作者：Shuai Wang、Jose A. Cuesta-Seijo、Alexander Striebeck、Dominique Lafont、Monica M. Palcic、Sébastien Vidal

  DOI：10.1002/cplu.201500282

  日期：2015.10

  provided modest glycosyltransferase inhibitors. The synthetic strategy employed a combination of glycosylation, amide bond formation and azide-alkyne "click" chemistry. Inhibition constants (Ki ) in the high micromolar range were obtained with a selection of five galactosyltransferases. Cocrystals of three inhibitors bound at the active site of a blood group A/B synthesizing glycosyltransferase were

  用丝氨酸类似物模拟核苷酸二磷酸糖的二磷酸部分提供了适度的糖基转移酶抑制剂。合成策略采用了糖基化，酰胺键形成和叠氮化物-炔烃“点击”化学的组合。通过选择五种半乳糖基转移酶，可获得高微摩尔范围内的抑制常数（Ki）。分析了在合成糖基转移酶的A / B血型的活性位点结合的三种抑制剂的共晶体。类似物的结构和抑制模式证明了酶的灵活性，这使糖基转移酶抑制剂的合理设计复杂化。
• Synthesis and biological evaluation of novel neamine–nucleoside conjugates potentially targeting to RNAs
  作者：Yanli Xu、Hongwei Jin、Zhenjun Yang、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.tet.2009.04.084

  日期：2009.7

  Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking Study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.