4-S-pivaloyloxymethyl-2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-4-thiouridine | 219709-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-S-pivaloyloxymethyl-2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-4-thiouridine
• 英文别名: [1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]sulfanylmethyl 2,2-dimethylpropanoate
• CAS: 219709-48-5
• 化学式: C₄₂H₅₄N₂O₉SSi
• 分子量: 791.05
• InChiKey: LCDRQMPQRVDYJX-UMHCDNJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  55.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127.57
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 4-S-pivaloyloxymethyl-2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-4-thiouridine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以69%的产率得到4-S-pivaloyloxymethyl-5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-4-thiouridine-3'-(cyanoethyl)-N,N'-diisopropyl-phosphoramidite
  参考文献：
  名称：

  Chemical Synthesis of 4-Thiouridine-Containing Substrate Analogues of tRNA:Pseudouridine-55 Synthase: Photocross-Linking Studies

  摘要：

  For site specific incorporation of 4-thiouridine into oligoribonucleotides a new phosphoramidite is proposed. It makes use of the S-pivaloyloxymethyl group for the protection of the thiol function. This group is easily introduced and removed without modification of the standard protocol for solid phase synthesis of RNA. Three 4-thiouridine-containing oligoribonucleotides (21-mers), corresponding to tRNA minisubstrates of yeast tRNA:pseudouridine-55 synthase (Pus4) were prepared. These 4-thiouridine containing substrates were characterized and used as photoaffinity probe of the enzyme:substrate complex. Irradiation resulted in the specific photocross-linking of these oligoribonucleotides with purified recombinant tRNA:pseudouridine-55 synthase.

  DOI：

  10.1080/07328319808004327
• 作为产物：
  描述：

  5'-O-dimethoxytrityl-4-thiouridine 在 咪唑 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 50.0h， 生成 4-S-pivaloyloxymethyl-2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-4-thiouridine
  参考文献：
  名称：

  Chemical Synthesis of 4-Thiouridine-Containing Substrate Analogues of tRNA:Pseudouridine-55 Synthase: Photocross-Linking Studies

  摘要：

  For site specific incorporation of 4-thiouridine into oligoribonucleotides a new phosphoramidite is proposed. It makes use of the S-pivaloyloxymethyl group for the protection of the thiol function. This group is easily introduced and removed without modification of the standard protocol for solid phase synthesis of RNA. Three 4-thiouridine-containing oligoribonucleotides (21-mers), corresponding to tRNA minisubstrates of yeast tRNA:pseudouridine-55 synthase (Pus4) were prepared. These 4-thiouridine containing substrates were characterized and used as photoaffinity probe of the enzyme:substrate complex. Irradiation resulted in the specific photocross-linking of these oligoribonucleotides with purified recombinant tRNA:pseudouridine-55 synthase.

  DOI：

  10.1080/07328319808004327