5-methylselanyl-2'-deoxyuridine | 1161403-61-7

• 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: 5-methylselanyl-2'-deoxyuridine
• 英文别名: 2'-deoxy-5-methylselenyluridine；5-seleno-thymidine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylselanylpyrimidine-2,4-dione
• CAS: 1161403-61-7
• 化学式: C₁₀H₁₄N₂O₅Se
• 分子量: 321.192
• InChiKey: DUFZFHRKFSDLIB-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.45
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methylselanyl-2'-deoxyuridine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 以82%的产率得到5-methylseleno-5’-O-(4,4-dimethoxytrityl)-2’-deoxyuridine
  参考文献：
  名称：

  Synthesis and Crystallographic Analysis of 5-Se-Thymidine DNAs

  摘要：

  We investigated the possibility of the interaction of 5-CH(3) of thymidine and its 5'-phosphate backbone (C-H...O(-)-PO(3) interaction) in DNA via the insertion of the atomic probe (a selenium atom) into the exo-5-position of thymidine (5-Se-T). 5-Se-T was synthesized for the first time, via Mn(OAc)(3) assisted electrophilic addition of CH(3)SeSeCH(3) to 3',5'-di-O-benzoyl-2'-deoxyuridine. The 5-Se-T phosphoramidite was subsequently synthesized and incorporated into DNA in over 99% coupling yield. Biophysical and structural investigations of the 5-Se-T DNAs revealed that the Se-modified and nonmodified DNAs are virtually identical. In addition, the crystallographic analysis of a 5-Se-T DNA strongly suggests a hydrogen-bond formation between the 5-CH(3) and 5'-phosphate groups (CH(3)...PO(4)(-) interaction).

  DOI：

  10.1021/ol9004867
• 作为产物：
  描述：

  3',5'-di-O-benzoyl-2'-deoxy-5-methylselenyluridine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到5-methylselanyl-2'-deoxyuridine
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS AND DERIVATIZATION OF DNAS AND RNAS ON THE NUCLEOBASES OF PYRIMIDINES FOR FUNCTION, STRUCTURE, AND THERAPEUTICS
  [FR] NOUVEAUX COMPOSÉS ET DÉRIVATION D'ADN ET D'ARN SUR LES NUCLÉOBASES DE PYRIMIDINES À DES FINS DE FONCTION, DE STRUCTURE ET DE THÉRAPEUTIQUE

  摘要：

  公开号：

  WO2010135564A3

文献信息

• Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides
  作者：Filip Botha、Michaela Slavíčková、Radek Pohl、Michal Hocek

  DOI：10.1039/c6ob01917j

  日期：——

  The syntheses of 5-arylsulfanyl- or 5-arylselanylpyrimidine and 7-arylsulfanyl- or 7-arylselanyl-7-deazapurine nucleosides and nucleotides were developed by the Cu-mediated sulfanylations or selanylations of the corresponding 5-iodopyrimidine or 7-iodo-7-deazapurine nucleosides or nucleotides with diaryldisulfides or -diselenides. The reactions were also applicable for direct modifications of 2′-deoxycytidine

  5-芳基硫烷基-或5-芳基硒基嘧啶和7-芳基硫烷基-或7-芳基硒基-7-脱氮嘌呤核苷和核苷酸的合成是通过相应的5-碘嘧啶或7-碘基-7-的铜介导的磺酰化或硒基化而开发的。脱氮嘌呤核苷或带有二芳基二硫化物或-二硒化物的核苷酸。该反应也可用于2'-脱氧胞苷三磷酸的直接修饰，并且所得的5-芳基硫烷基或5-芳基硒基-dCTP用作聚合酶合成底物的底物，所述DNA在主要凹槽中带有芳基硫烷基或芳基硒基。