5'-(3-hydroxy-propyl)amino-5'-deoxy-guanosine | 142468-34-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-(3-hydroxy-propyl)amino-5'-deoxy-guanosine
• 英文别名: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(3-hydroxypropylamino)methyl]oxolan-2-yl]-1H-purin-6-one
• CAS: 142468-34-6
• 化学式: C₁₃H₂₀N₆O₅
• 分子量: 340.339
• InChiKey: PEWJYWYFTYYHMI-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  167
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N²-acetylguanosine 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 反应 168.0h， 生成 5'-(3-hydroxy-propyl)amino-5'-deoxy-guanosine
  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

文献信息

• Inhibitors of GDP-mannose dehydrogenase of Pseudomonas aeruginosa mucoid strains
  作者：N Elloumi、B Moreau、L Aguiar、N Jaziri、M Sauvage、C Hulen、ML Capmau

  DOI：10.1016/0223-5234(92)90103-8

  日期：1992.3

  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.