5′-O-[N-(valinyl)sulfamoyl]adenosine | 312493-34-8

• 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-(valinyl)sulfamoyl]adenosine
• 英文别名: Val-AMS；L-Val-AMS；5'-O-[N-[L-valyl]-sulfamoyl]adenosine；5'-O-(N-valinylsulfamoyl)adenosine；5'-O-[(N-L-valinyl)sulfamoyl]adenosine；(1Z,2S)-N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxysulfonyl]-2-azaniumyl-3-methylbutanimidate
• CAS: 312493-34-8
• 化学式: C₁₅H₂₃N₇O₇S
• 分子量: 445.456
• InChiKey: TXCZGHBHNXNXMA-CYUGOOACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  226
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5′-O-[N-(valinyl)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 [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S,3R)-2-[[(2S)-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]pentanoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoyl]amino]acetyl]amino]-4-oxo-4-(tritylamino)butanoyl]amino]propanoyl]amino]-3-methylbutanoyl]sulfamate
  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 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 triethylamine tris(hydrogen fluoride) 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 5′-O-[N-(valinyl)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

文献信息

• Solid-Phase Synthesis of 5′-O-[N-(Acyl)sulfamoyl]adenosine Derivatives
  作者：Itedale Namro Redwan、Hanna Jacobson Ingemyr、Thomas Ljungdahl、Christopher P. Lawson、Morten Grøtli

  DOI：10.1002/ejoc.201200329

  日期：2012.7

  The solid-phase synthesis of 5'-O-[N-(acyl)sulfamoyl]adenosine derivatives is described. The use of a Rink amide polystyrene solid support together with an appropriately protected ribo-purine starting material allowed for the development of a highly reliable and practical route for the solid-phase synthesis of 5'-O-[N-(acyl)sulfamoyl]adenosines. The developed procedure enables the efficient parallel

  描述了 5'-O-[N-（酰基）氨磺酰基] 腺苷衍生物的固相合成。使用 Rink 酰胺聚苯乙烯固体载体和适当保护的核糖嘌呤起始材料，为 5'-O-[N-(酰基)氨磺酰基]的固相合成开发了一种高度可靠和实用的路线腺苷。开发的程序能够以高产率高效并行合成目标化合物。这些化合物是酰基腺苷酸的不可水解等排体，它们在一系列不同的代谢途径中发挥重要作用，例如核糖体和非核糖体肽合成、脂肪酸氧化或酶调节；一些形成腺苷酸的酶是潜在的药物靶点。
• Investigation, optimization and synthesis of sulfamoyloxy-linked aminoacyl-AMP analogues
  作者：Itedale Namro Redwan、Thomas Ljungdahl、Morten Grøtli

  DOI：10.1016/j.tet.2011.12.011

  日期：2012.2

  Aminoacyl-tRNA synthetases (aaRSs) constitute a family of enzymes that transfer amino acids to their corresponding tRNA molecules to form aminoacyl-tRNAs and have been validated as potential drug targets. Sulfamoyloxy-linked aminoacyl-AMP analogues are potent inhibitors of aaRSs. In this article, we report the synthesis of several new sulfamoyl analogues of as-AMP that up to now have been difficult or even impossible to prepare with current synthetic strategies. The developed synthetic strategy relies on performing the synthesis under neutral conditions followed by global deprotection using catalytic hydrogenation affording the desired 5'-0-(N-aminoacyl)sulfamoyladenosine compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• Extended targeting potential and improved synthesis of Microcin C analogs as antibacterials
  作者：Gaston H.M. Vondenhoff、Svetlana Dubiley、Konstantin Severinov、Eveline Lescrinier、Jef Rozenski、Arthur Van Aerschot

  DOI：10.1016/j.bmc.2011.07.052

  日期：2011.9

  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.