5'-O-[N-[L-aspartyl(O-tert-butyl)]-sulfamoyl]adenosine | 1341125-29-8

• 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-[N-[L-aspartyl(O-tert-butyl)]-sulfamoyl]adenosine
• CAS: 1341125-29-8
• 化学式: C₁₈H₂₇N₇O₉S
• 分子量: 517.52
• InChiKey: SXJDZDATDHHIOO-XBMNBGRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  244.1
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  5'-O-[N-[L-aspartyl(O-tert-butyl)]-sulfamoyl]adenosine 、 formyl-methionyl-arginyl(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-threonyl(tBu)-glycyl-asparaginyl(trityl)-alanyl-OH 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Extended targeting potential and improved synthesis of Microcin C analogs as antibacterials

  摘要：

  Microcin C (McC) (1) is a potent antibacterial compound produced by some Escherichia coli strains. McC functions through a Trojan-Horse mechanism: it is actively taken up inside a sensitive cell through the function of the YejABEF-transporter and then processed by cellular aminopeptidases. Processed McC (2) is a non-hydrolysable aspartyl-adenylate analog that inhibits aspartyl-tRNA synthetase (AspRS). A new synthesis is described that allows for the production of a wide variety of McC analogs in acceptable amounts. Using this synthesis a number of diverse compounds was synthesized with altered target specificity. Further characteristics of the YejABEF transporters were determined using these compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.052
• 作为产物：
  描述：

  在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以88%的产率得到5'-O-[N-[L-aspartyl(O-tert-butyl)]-sulfamoyl]adenosine
  参考文献：
  名称：

  Extended targeting potential and improved synthesis of Microcin C analogs as antibacterials

  摘要：

  Microcin C (McC) (1) is a potent antibacterial compound produced by some Escherichia coli strains. McC functions through a Trojan-Horse mechanism: it is actively taken up inside a sensitive cell through the function of the YejABEF-transporter and then processed by cellular aminopeptidases. Processed McC (2) is a non-hydrolysable aspartyl-adenylate analog that inhibits aspartyl-tRNA synthetase (AspRS). A new synthesis is described that allows for the production of a wide variety of McC analogs in acceptable amounts. Using this synthesis a number of diverse compounds was synthesized with altered target specificity. Further characteristics of the YejABEF transporters were determined using these compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.052