8.5'-Anhydro-8-oxoadenosin-2'.3'-cyclo-phosphat | 52482-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8.5'-Anhydro-8-oxoadenosin-2'.3'-cyclo-phosphat
• 英文别名: O^{2'_,O3'_{-hydroxyphosphoryl-8,O}5'}-cyclo-adenosine；(4R)-8-amino-2-oxo-(3at,13at)-4,5,13,13a-tetrahydro-3aH-2λ⁵-4r,13c-epioxido-[1,3,2]dioxaphospholo[4',5':5,6][1,3]oxazocino[3,2-e]purin-2-ol
• CAS: 52482-86-7
• 化学式: C₁₀H₁₀N₅O₆P
• 分子量: 327.193
• InChiKey: GCISCMPNFHSLJH-HAVMAKPUSA-N

反应信息

• 作为反应物：
  描述：

  8.5'-Anhydro-8-oxoadenosin-2'.3'-cyclo-phosphat 生成 N⁶,2'-O-Dibenzoyl-8.5'-anhydro-8-oxyadenosin
  参考文献：
  名称：

  Polynucleotides. XX. Synthesis of an AUG Analog containing 8, 5'-O-Cycloadenosine

  摘要：

  8, 5'-Anhydro-8-oxyadenosine was phosphorylated using cyanoethylphosphate and dicyclohexylcarbodiimide (DCC) in dimethylformamide-pyridine. Treatment of the products with a mixture of 50% aqueous pyridine-triethylamine and DEAE-cellulose chromatography gave 2', 3'-cyclic phosphate in a yield of 48%. 8, 5'-Anhydro-8-oxyadenosine 3'-phosphate was obtained by RNase M digestion of the cyclic phosphate. After protection with benzoic anhydride in tetraethylammonium benzoate buffer, the 3'-phosphate was condensed with 2'-O-benzoyluridylyl-(3'→5')-N2, 2', 3'-O-triisobutyrylguanosine by the use of DCC. DEAE-cellulose, Sephadex G-25 and G-15 column chromatography gave 8, 5'-anhydro-8-oxyadenylyl-(3'→5')-uridylyl-(3'→5')-guanosine. The trinucleotide was characterized by degradation to cyclo Ap, Up and G with RNase M.

  DOI：

  10.1248/cpb.22.123
• 作为产物：
  描述：

  5',8-O-Cycloadenosine 在 吡啶 、 2-氰基乙基磷酸二氢盐 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 8.5'-Anhydro-8-oxoadenosin-2'.3'-cyclo-phosphat
  参考文献：
  名称：

  Polynucleotides. XX. Synthesis of an AUG Analog containing 8, 5'-O-Cycloadenosine

  摘要：

  8, 5'-Anhydro-8-oxyadenosine was phosphorylated using cyanoethylphosphate and dicyclohexylcarbodiimide (DCC) in dimethylformamide-pyridine. Treatment of the products with a mixture of 50% aqueous pyridine-triethylamine and DEAE-cellulose chromatography gave 2', 3'-cyclic phosphate in a yield of 48%. 8, 5'-Anhydro-8-oxyadenosine 3'-phosphate was obtained by RNase M digestion of the cyclic phosphate. After protection with benzoic anhydride in tetraethylammonium benzoate buffer, the 3'-phosphate was condensed with 2'-O-benzoyluridylyl-(3'→5')-N2, 2', 3'-O-triisobutyrylguanosine by the use of DCC. DEAE-cellulose, Sephadex G-25 and G-15 column chromatography gave 8, 5'-anhydro-8-oxyadenylyl-(3'→5')-uridylyl-(3'→5')-guanosine. The trinucleotide was characterized by degradation to cyclo Ap, Up and G with RNase M.

  DOI：

  10.1248/cpb.22.123