3',5'-di-O-acetyl-2'-O-methyluridine | 61671-79-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-di-O-acetyl-2'-O-methyluridine
• 英文别名: [(2R,3R,4R,5R)-3-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-methoxyoxolan-2-yl]methyl acetate
• CAS: 61671-79-2
• 化学式: C₁₄H₁₈N₂O₈
• 分子量: 342.306
• InChiKey: ZMFJISRUWRKIOE-OJAKKHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-2'-O-methyluridine 在 双(乙腈)氯化钯(II) 咪唑 、 四氧化锇 、 氯化亚砜 、 N-甲基吲哚酮 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 57.25h， 生成 1-[3,5-bis-O-(tert-butyldimethylsilyl)-2-O-methyl-β-D-ribo-furanosyl]-6-(1,2-dihydroxyethyl)-4-ethoxy-2-pyrimidinone
  参考文献：
  名称：

  Introduction of 6-Formylcytidine into a Myb Binding Sequence

  摘要：

  Single 6-formylcytidine was introduced into a oligonucleotide duplex (23 mers) as a substitute for thymidine in the Myb binding sequence of 3'-TTGAC-5'. The modified duplex showed Tm of 67 degrees C, which was six degrees lower than the Tm of the native duplex. Binding affinity of the 23-mers to the Myb protein was estimated by electrophoretic mobility shift assays, and the binding was almost completely abolished.

  DOI：

  10.1080/07328319908044640
• 作为产物：
  描述：

  2,2'-脱水尿苷 在 吡啶 、 硼酸三甲酯 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 3',5'-di-O-acetyl-2'-O-methyluridine
  参考文献：
  名称：

  Introduction of 6-Formylcytidine into a Myb Binding Sequence

  摘要：

  Single 6-formylcytidine was introduced into a oligonucleotide duplex (23 mers) as a substitute for thymidine in the Myb binding sequence of 3'-TTGAC-5'. The modified duplex showed Tm of 67 degrees C, which was six degrees lower than the Tm of the native duplex. Binding affinity of the 23-mers to the Myb protein was estimated by electrophoretic mobility shift assays, and the binding was almost completely abolished.

  DOI：

  10.1080/07328319908044640

文献信息

• [EN] NUCLEIC ACID CHEMICAL MODIFICATIONS<br/>[FR] MODIFICATIONS CHIMIQUES D'ACIDE NUCLÉIQUE
  申请人：ALNYLAM PHARMACEUTICALS INC

  公开号：WO2010101951A1

  公开（公告）日：2010-09-10

  he present invention provides nucleosides of formula (1) and oligonucleotides comprising at least on nucleoside of formula (2): Another aspect of the invention relates to a method of inhibiting the expression of a gene in cell, the method comprising (a) contacting an oligonucleotide of the invention with the cell; and (b) maintaining the cell from step (a) for a time sufficient to obtain degradation of the mRNA of the target gene.

  本发明提供了式（1）的核苷和包含至少一种式（2）核苷的寡核苷酸；发明的另一个方面涉及一种抑制细胞中基因表达的方法，该方法包括（a）将本发明的寡核苷酸与细胞接触；和（b）维持步骤（a）中的细胞足够长的时间以获得目标基因mRNA的降解。
• Chemical synthesis of methoxy nucleosides
  申请人：Ribozyme Pharmaceuticals, Inc.

  公开号：US20030204078A1

  公开（公告）日：2003-10-30

  Process for chemical synthesis of methoxy nucleosides.

  甲氧基核苷化合物的化学合成过程。
• Synthesis of methoxy nucleosides and enzymatic nucleic acid molecules
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP1108724A2

  公开（公告）日：2001-06-20

  This invention relates to chemical synthesis of 2'-O-methyl, 3'-O-methyl and 5'-O-methyl nucleosides, incorporation of novel chemical modifications in enzymatic nucleic acid molecules and improved methods for the synthesis of enzymatic nucleic acid molecules.

  本发明涉及 2'-O-甲基、3'-O-甲基和 5'-O-甲基核苷的化学合成、在酶核酸分子中加入新型化学修饰以及改进酶核酸分子的合成方法。
• [EN] NON-NATURAL RIBONUCLEOTIDES, AND METHODS OF USE THEREOF<br/>[FR] RIBONUCLÉOTIDES NON NATURELS, ET PROCÉDÉS POUR LES UTILISER
  申请人：ALNYLAM PHARMACEUTICALS INC

  公开号：WO2009120878A3

  公开（公告）日：2009-11-19
• Synthesis and solution conformation studies of the modified nucleoside N4,2′-O-dimethylcytidine (m4Cm) and its analogues
  作者：Santosh K. Mahto、Christine S. Chow

  DOI：10.1016/j.bmc.2008.09.016

  日期：2008.10

  The dimethylated ribosomal nucleoside m(4)Cm and its monomethylated analogues Cm and m(4)C were synthesized. The conformations (syn vs anti) of the three modified nucleosides and cytidine were determined by CD and 1D NOE difference spectroscopy. The ribose sugar puckers were determined by the use of proton coupling constants. The position of modi. cation (e. g., O vs N methylation) was found to have an effect on the sugar pucker of cytidine. (C) 2008 Elsevier Ltd. All rights reserved.