N⁶-L-lysyl-L-lysine | 94613-75-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N⁶-L-lysyl-L-lysine
• 英文别名: L-lysine-Nε-L-lysine；N~6~-L-Lysyl-L-Lysine；(2S)-2-amino-6-[[(2S)-2,6-diaminohexanoyl]amino]hexanoic acid
• CAS: 94613-75-9
• 化学式: C₁₂H₂₆N₄O₃
• 分子量: 274.363
• InChiKey: ISWYJQKGNGBKJG-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁶-L-lysyl-L-lysine 在 N-甲基吗啉 、 碳酸氢钠 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 N-{N^6'-[N^2",N^6"-bis(2,3-diacetoxybenzoyl)-L-lysyl]-N^2'-(2,3-diacetoxybenzoyl)-L-lysyl}-ampicillin sodium salt
  参考文献：
  名称：

  New synthetic siderophores and Their β-Lactam conjugates based on diamino acids and dipeptides

  摘要：

  Linking of siderophores to antibiotics improves the penetration and therefore increases the antibacterial activity of the antibiotics. We synthesized the acylated catecholates and hydroxamates as siderophore components for antibiotic conjugates to reduce side effects of unprotected catecholate and hydroxamate moieties. In this paper, we report on bis- and tris-catecholates and mixed catecholate hydroxamates based on diamino acids or dipeptides. These compounds were active as siderophores in a growth promotion assay under iron limitation. Most of the conjugates with beta-lactams showed high in vitro activity against Gram-negative bacteria especially Pseudomonas acruginosa, Escherichia coli, Klebsiella pneumoniae, Serratia mareeseems and Stenotrophomonas maltophilia. The compounds with enhanced antibacterial activity use active iron uptake routes to penetrate the bacterial outer membrane barrier, demonstrated by assays with mutants deficient in components of the iron transport system. Correlation between chemical structure and biological activity was studied. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00044-5
• 作为产物：
  描述：

  (S)-2,6-二叔丁氧羰基氨基己酸 、 N-α-(tert-butoxycarbonyl)-L-lysine methyl ester 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 ammonium hydroxide 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 N⁶-L-lysyl-L-lysine
  参考文献：
  名称：

  吡咯赖氨酸合酶（PylD）催化的氨基酸中吡咯啉和四氢吡啶环的形成

  摘要：

  脱氢酶PylD通过将异肽L-赖氨酸-Nε -3 R-甲基-D-鸟氨酸转化为22个蛋白氨基酸来催化吡咯赖氨酸途径的最终步骤。在这项研究中，我们证明了如何结合化学合成，酶动力学和X射线晶体学方法，利用PylD将各种异肽氧化为新氨基酸。该数据使得能够详细描述作为吡咯赖氨酸类似物的成分的吡咯啉和四氢吡啶环的生物合成的PylD反应轨迹。

  DOI：

  10.1002/anie.201402595

文献信息

• New synthetic siderophores and Their β-Lactam conjugates based on diamino acids and dipeptides
  作者：S Wittmann

  DOI：10.1016/s0968-0896(02)00044-5

  日期：2002.6

  Linking of siderophores to antibiotics improves the penetration and therefore increases the antibacterial activity of the antibiotics. We synthesized the acylated catecholates and hydroxamates as siderophore components for antibiotic conjugates to reduce side effects of unprotected catecholate and hydroxamate moieties. In this paper, we report on bis- and tris-catecholates and mixed catecholate hydroxamates based on diamino acids or dipeptides. These compounds were active as siderophores in a growth promotion assay under iron limitation. Most of the conjugates with beta-lactams showed high in vitro activity against Gram-negative bacteria especially Pseudomonas acruginosa, Escherichia coli, Klebsiella pneumoniae, Serratia mareeseems and Stenotrophomonas maltophilia. The compounds with enhanced antibacterial activity use active iron uptake routes to penetrate the bacterial outer membrane barrier, demonstrated by assays with mutants deficient in components of the iron transport system. Correlation between chemical structure and biological activity was studied. (C) 2002 Published by Elsevier Science Ltd.
• The Formation of Pyrroline and Tetrahydropyridine Rings in Amino Acids Catalyzed by Pyrrolysine Synthase (PylD)
  作者：Felix Quitterer、Philipp Beck、Adelbert Bacher、Michael Groll

  DOI：10.1002/anie.201402595

  日期：2014.7.28

  The dehydrogenase PylD catalyzes the ultimate step of the pyrrolysine pathway by converting the isopeptide L‐lysine‐Nε‐3R‐methyl‐D‐ornithine to the 22nd proteinogenic amino acid. In this study, we demonstrate how PylD can be harnessed to oxidize various isopeptides to novel amino acids by combining chemical synthesis with enzyme kinetics and X‐ray crystallography. The data enable a detailed description

  脱氢酶PylD通过将异肽L-赖氨酸-Nε -3 R-甲基-D-鸟氨酸转化为22个蛋白氨基酸来催化吡咯赖氨酸途径的最终步骤。在这项研究中，我们证明了如何结合化学合成，酶动力学和X射线晶体学方法，利用PylD将各种异肽氧化为新氨基酸。该数据使得能够详细描述作为吡咯赖氨酸类似物的成分的吡咯啉和四氢吡啶环的生物合成的PylD反应轨迹。