Thymidine, P-[2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl]-P,P-dithiothymidylyl-(3a(2)a5a(2))- | 190062-29-4

• 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: Thymidine, P-[2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl]-P,P-dithiothymidylyl-(3a(2)a5a(2))-
• 英文别名: 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] 2,2-dimethylpropanethioate
• CAS: 190062-29-4
• 化学式: C₂₇H₃₉N₄O₁₁PS₃
• 分子量: 722.799
• InChiKey: KLSNJODPEZTSCL-VNXCAFLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  276
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Thymidine, P-[2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl]-P,P-dithiothymidylyl-(3a(2)a5a(2))- 在 水 作用下， 生成 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
  参考文献：
  名称：

  The pro-oligonucleotide approach. V: Influence of the phosphorus atom environment on the hydrolysis of enzymolabile dinucleoside phosphotriesters

  摘要：

  Six dithymidine phosphotriester analogs bearing an enzymolabile phosphate proctecting group were synthesized in order to select the most appropriate model for the prooligonucleotide approach. Series (1) under bar and (3) under bar were chosen on the basis of their stability in culture medium and their capacity, when incubated in total cell extract, to deliver selectively dithymidine phosphodiester and phosphorothioate diester respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00106-6
• 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 、 S-(2-iodoethyl) 2,2-dimethylpropanethioate 在 phosphate buffer 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 Thymidine, P-[2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl]-P,P-dithiothymidylyl-(3a(2)a5a(2))-
  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