bis-4-thio-2'-deoxyuridine | 22969-02-4

• 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: bis-4-thio-2'-deoxyuridine
• 英文别名: Bis-<1-(2-desoxy-β-D-ribofuranosyl)-2-oxo-1,2-dihydro-pyrimidinyl-(4)>-disulfid；1,1'-bis-(β-D-erythro-2-deoxy-pentofuranosyl)-1H,1'H-4,4'-disulfanediyl-bis-pyrimidin-2-one；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-[[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]disulfanyl]pyrimidin-2-one
• CAS: 22969-02-4
• 化学式: C₁₈H₂₂N₄O₈S₂
• 分子量: 486.527
• InChiKey: JXOBNNPRFXXWFV-PHEULEMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  215
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2'-deoxy-4-thiouridine 在 碘 、 potassium iodide 作用下， 以 phosphate buffer 为溶剂， 反应 0.25h， 以91%的产率得到bis-4-thio-2'-deoxyuridine
  参考文献：
  名称：

  Thionucleoside disulfides as covalent constraints of DNA conformation

  摘要：

  Full details of a new strategy for cross-linking of duplex oligonucreotides are described. A direct base-to-base disulfide bond is formed by oxidation of two appropriately positioned thionucleoside bases. Cross-link formation between 4-thio-2'-deoxyuridine and 6-thio-2'-deoxyinosine is demonstrated in three sequence contexts (3' to 3', 5' to 5', and opposed). Disulfide formation occurs in high yield in both duplex and hairpin DNA. Molecular modeling and circular dichroism were used to demonstrate minimal distortion of the constrained B-DNA double helix. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00704-8