5',8-O-Cycloadenosine | 30737-86-1

• 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: 5',8-O-Cycloadenosine
• 英文别名: 8,O^5'-cyclo-adenosine；(8R)-4-amino-8,9,10,11-tetrahydro-7H-8r,11c-epioxido-[1,3]oxazocino[3,2-e]purine-9c,10c-diol
• CAS: 30737-86-1；34210-52-1
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: KLOSTTZWIGTDEO-HAVMAKPUSA-N

物化性质

• 沸点：
  638.0±65.0 °C(Predicted)
• 密度：
  2.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.58
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  128.54
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  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