5'-O-<<<<(2'',3'',4'',6''-tetra-O-acetyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylidene-N2-acetylguanosine | 142468-36-8

• 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'-O-<<<<(2'',3'',4'',6''-tetra-O-acetyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylidene-N2-acetylguanosine
• 英文别名: 5'-O-<<<<(2'',3'',4'',6''-tetra-O-acetyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylidene-N²-acetylguanosine
• CAS: 142468-36-8
• 化学式: C₃₀H₃₈N₆O₁₉S
• 分子量: 818.727
• InChiKey: RDXSQMAZPAWBMW-JPPLYACVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  56.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  316.49
• 氢给体数：
  3.0
• 氢受体数：
  22.0

反应信息

• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基吡喃己糖 在 吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 5'-O-<<<<(2'',3'',4'',6''-tetra-O-acetyl-α-D-mannopyranosyl)oxy>carbonyl>amino>sulfonyl>-2',3'-O-isopropylidene-N2-acetylguanosine
  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