tert-butyl (S)-4-(((((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methoxy)sulfonyl)amino)-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate | 1341125-27-6

• 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: tert-butyl (S)-4-(((((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methoxy)sulfonyl)amino)-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate
• CAS: 1341125-27-6
• 化学式: C₃₈H₆₁N₇O₁₁SSi₂
• 分子量: 880.18
• InChiKey: YPZDNMDBNCOAQG-XVCYAKCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  59.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  234.41
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-4-(((((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methoxy)sulfonyl)amino)-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以76%的产率得到
  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：

  ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl sulfamate 、 N-苄氧羰基-L-天冬氨酸4-叔丁酯1-(N-琥珀酰亚胺)酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以90%的产率得到tert-butyl (S)-4-(((((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methoxy)sulfonyl)amino)-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate
  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