5′-O-N-(L-methionyl)sulfamoyladenosine triethylammonium salt | 1122489-97-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 5′-O-N-(L-methionyl)sulfamoyladenosine triethylammonium salt
• 英文别名: 5'-O-(N-L-methionyl)-sulfamoyladenosine triethylamine salt；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-[(2S)-2-amino-4-methylsulfanylbutanoyl]sulfamate;N,N-diethylethanamine
• CAS: 1122489-97-7
• 化学式: C₆H₁₅N*C₁₅H₂₃N₇O₇S₂
• 分子量: 578.714
• InChiKey: YPEYLEYIHWQLLH-OHKGGWSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.17
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  221.04
• 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-methionyl)sulfamoyladenosine triethylammonium salt 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 5'-O-[N-(N-L-alanyl)-L-methionyl]-sulfamoyladenosine triethylamine salt
  参考文献：
  名称：

  Antibacterial 5′-O-(N-dipeptidyl)-sulfamoyladenosines

  摘要：

  The aminoacyl-tRNA synthetase (aaRS) class of enzymes is a validated target for antimicrobial development. Aminoacyl analogues of 5'-O-(N-L-aminoacyl)-sulfamoyladenosines are known to be potent inhibitors of aaRS, but whole cell antibacterial activity of these compounds is very limited, and poor penetration into bacteria has been proposed as the main reason for this. Aiming to find derivatives that better penetrate bacteria, we developed a simple and short method to prepare dipeptidyl-derivatives of 5'-O-(N-L-aminoacyl)-sulfamoyladenosines, and used this method to prepare 18 5'-O-(N-dipeptidyl)-sulfamoyladenosines. The antibacterial activity of these derivatives and a number of reference compounds against S. aureus, E. faecalis and E. coli was determined. Several of the new derivatives showed improved antibacterial activity and an altered spectrum of antibacterial activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.054
• 作为产物：
  描述：

  叔丁氧羰基-蛋氨酰-琥珀酰亚胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5′-O-N-(L-methionyl)sulfamoyladenosine triethylammonium salt
  参考文献：
  名称：

  Antibacterial 5′-O-(N-dipeptidyl)-sulfamoyladenosines

  摘要：

  The aminoacyl-tRNA synthetase (aaRS) class of enzymes is a validated target for antimicrobial development. Aminoacyl analogues of 5'-O-(N-L-aminoacyl)-sulfamoyladenosines are known to be potent inhibitors of aaRS, but whole cell antibacterial activity of these compounds is very limited, and poor penetration into bacteria has been proposed as the main reason for this. Aiming to find derivatives that better penetrate bacteria, we developed a simple and short method to prepare dipeptidyl-derivatives of 5'-O-(N-L-aminoacyl)-sulfamoyladenosines, and used this method to prepare 18 5'-O-(N-dipeptidyl)-sulfamoyladenosines. The antibacterial activity of these derivatives and a number of reference compounds against S. aureus, E. faecalis and E. coli was determined. Several of the new derivatives showed improved antibacterial activity and an altered spectrum of antibacterial activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.054

文献信息

• Functional profiling of adenylation domains in nonribosomal peptide synthetases by competitive activity-based protein profiling
  作者：Shota Kasai、Sho Konno、Fumihiro Ishikawa、Hideaki Kakeya

  DOI：10.1039/c5cc04953a

  日期：——

  Using a library of sulfamoyloxy-linked aminoacyl-AMP analogs, we describe competitive activity-based protein profiling to facilitate directly the functional prediction and assessment of adenylation domains in nonribosomal peptide synthetases in proteomic environments.

  利用磺胺氧基连接的氨酰-AMP类似物库，我们描述了竞争性活性蛋白质分析技术，以直接促进在蛋白质组学环境中对非核糖体肽合成酶中腺苷化结构域的功能预测和评估。