2'-O-(2-methoxyethyl)-5-iodouridine | 1251827-55-0

• 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: 2'-O-(2-methoxyethyl)-5-iodouridine
• 英文别名: io5Ura-MeOEt(-2)Ribf；1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-(2-methoxyethoxy)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 1251827-55-0
• 化学式: C₁₂H₁₇IN₂O₇
• 分子量: 428.181
• InChiKey: VQSZOGGQNKCHPG-TURQNECASA-N

物化性质

• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-O-(2-methoxyethyl)-5-iodouridine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 以98%的产率得到2'-O-(2-methoxyethyl)-5'-O-(4,4'-dimethoxytrityl)-5-iodouridine
  参考文献：
  名称：

  Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

  摘要：

  2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from D-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.005
• 作为产物：
  描述：

  2'-O-(2-methoxyethyl)-3',5'-di-O-benzoyl-5-iodouridine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.75h， 以68%的产率得到2'-O-(2-methoxyethyl)-5-iodouridine
  参考文献：
  名称：

  Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

  摘要：

  2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from D-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.005