S-[2-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyl]sulfanylethyl] benzenecarbothioate

• 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: S-[2-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyl]sulfanylethyl] benzenecarbothioate
• 化学式: C₂₉H₃₅N₄O₁₁PS₃
• 分子量: 742.789
• InChiKey: IOPGCCJOYUXVAV-CMVLJIPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  276
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1-[(2R,4S,5R)-4-hydroxy-5-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-sulfidophosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 、 Thiobenzoic acid S-(2-iodo-ethyl) ester 在 phosphate buffer 作用下， 以 乙腈 为溶剂， 反应 118.0h， 生成 S-[2-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyl]sulfanylethyl] benzenecarbothioate
  参考文献：
  名称：

  The prooligonucleotide approach. III: Synthesis and bioreversibility of a chimeric phosphorodithioate prooligonucleotide

  摘要：

  Alkylation of a central gap of three phosphorodithioate linkages into a dodecathymidine methylphosphonate with methylacylthioethyl iodide (Me-SATE-I) yielded the corresponding neutral oligonucleotide. Upon incubation of the resulting non ionic prooligonucleotide in cell extracts, the bioreversible Me-SATE masking groups were selectively removed by carboxyesterases present in the milieu.

  DOI：

  10.1016/0960-894x(96)00051-0

文献信息

• The prooligonucleotide approach. III: Synthesis and bioreversibility of a chimeric phosphorodithioate prooligonucleotide
  作者：Guilem Tosquellas、Isabelle Barber、François Morvan、Bernard Rayner、Jean-Louis Imbach

  DOI：10.1016/0960-894x(96)00051-0

  日期：1996.2

  Alkylation of a central gap of three phosphorodithioate linkages into a dodecathymidine methylphosphonate with methylacylthioethyl iodide (Me-SATE-I) yielded the corresponding neutral oligonucleotide. Upon incubation of the resulting non ionic prooligonucleotide in cell extracts, the bioreversible Me-SATE masking groups were selectively removed by carboxyesterases present in the milieu.