5'-amino-5'-deoxy-N²-2',3'-O-triacetylguanosine | 142468-32-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5'-amino-5'-deoxy-N²-2',3'-O-triacetylguanosine
• CAS: 142468-32-4
• 化学式: C₁₆H₂₀N₆O₇
• 分子量: 408.371
• InChiKey: VWCGAYLGHBYDJD-SDBHATRESA-N

物化性质

• 密度：
  1.72±0.1 g/cm3(Predicted)

反应信息

• 作为产物：
  描述：

  5'-azido-5'-deoxy-N²-2',3'-O-triacetylguanosine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以77%的产率得到5'-amino-5'-deoxy-N²-2',3'-O-triacetylguanosine
  参考文献：
  名称：

  Inhibitors of GDP-mannose dehydrogenase of Pseudomonas aeruginosa mucoid strains

  摘要：

  The synthesis of 5'-amino-5'-deoxy guanosine was improved in order to use it for elaboration of liposolubles GDP-mannose analogues. GDP-mannose is the substrate of GDP-mannose dehydrogenase, a key enzyme in the alginates biosynthetic pathway of Pseudomonas aeruginosa mucoid strains. Guanosine, 5'-amino-5'-deoxy-guanosine, 5'-(3-hydroxypropyl)-amino-5'-deoxy-guanosine and 2 GDP mannose analogues were tested on the GDP mannose dehydrogenase activity. The more potent inhibitor was the GDP-mannose analogue where mannose is substituted by a 6-ethynyl derivative, linked to an N2-acetyl-2', 3'-O-isopropylidene guanosine by a sulfonyl amino carbonyl arm. As a hypothesis, this compound could be a suicide or irreversible inhibitor for the enzyme.

  DOI：

  10.1016/0223-5234(92)90103-8