N⁶-L-lysyl-N²-(ε-aminocaproyl)-L-lysine | 452303-42-3

• 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-N²-(ε-aminocaproyl)-L-lysine
• 英文别名: (2S)-2-(6-aminohexanoylamino)-6-[[(2S)-2,6-diaminohexanoyl]amino]hexanoic acid
• CAS: 452303-42-3
• 化学式: C₁₈H₃₇N₅O₄
• 分子量: 387.523
• InChiKey: LMBPJZJQSDQPEZ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-di(methoxycarbonyloxy)benzoyl chloride 、 N⁶-L-lysyl-N²-(ε-aminocaproyl)-L-lysine 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以50%的产率得到N²-[ε-(8-methoxycarbonyloxy-3,4-dihydro-2,4-dioxo-1,3-benzoxazin-3-yl)-n-hexanoyl]-N⁶-[2,6-bis(8-methoxycarbonyloxy-3,4-dihydro-2,4-dioxo-1,3-benzoxazin-3-yl)-n-hexanoyl]-L-lysine
  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：

  N-苄氧羰基--6-氨基己酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 N⁶-L-lysyl-N²-(ε-aminocaproyl)-L-lysine
  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

文献信息

• [DE] SIDEROPHORANALOGA ALS 4-ODER 6-ZÄHNIGE EISENCHELATOREN AUF DER BASIS VON AMINOSÄUREN ODER PEPTIDEN, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE ANWENDUNG<br/>[EN] SIDEROPHORE ANALOGUES AS TETRA- OR HEXADENTATE IRON CHELATORS ON THE BASIS OF AMINO ACIDS OR PEPTIDES, METHOD FOR PRODUCING THEM AND THE USE THEREOF<br/>[FR] ANALOGUES DE SIDEROPHORES EN TANT QUE CHELATEURS DU FER A 4 OU 6 DENTS, A BASE D'ACIDES AMINES OU DE PEPTIDES, PROCEDES DE PRODUCTION ET UTILISATIONS ASSOCIES
  申请人：GRUENENTHAL GMBH

  公开号：WO2002070545A2

  公开（公告）日：2002-09-12

  Die Erfindung betrifft neue Siderophoranaloga als 4- oder 6-zähnige Eisenchelatoren bzw. deren Acylderivate auf der Basis von Aminosäuren bzw. Peptiden der allgemeinen Formel I. Die erfindungsgemässen Verbindungen sind bei Mykobakterien sowie Gram-negativen Bakterienstämmen, insbesondere Pseudomonaden, E.coli- und Salmonella-Stämmen, als Siderophore wirksam. Sie können als Transportvehikel zur Einschleusung von Wirkstoffen, z.B. Antibiotika (als 'Siderophor-Antibiotikakonjugate') in Bakterienzellen dienen und damit deren antibakterielle Wirksamkeit verbessern bzw. erweitern sowie Resistenzen überwinden. Ausserdem sind die genannten Verbindungen als potentielle Prodrugformen für Eisenchelatoren geeignet zur Verwendung bei Erkrankungen, die auf einer Störung des Eisenstoffwechsels beruhen. (I), wobei R1 = OH bzw. ein zweites Aminosäuremolekül oder verschiedene Catechol-oder Hydroxamat-haltige Substituenten als weitere Chelatgruppen, R2 = H, Acyl oder -CO- in Verbindung mit R5, R3 = H, oder Acyl, R4 = H, Halogen oder verschiedene C- bzw. O-haltige Substituenten, R5 = H oder -CO- in Verbindung mit R2 bedeuten und die Verbindungen als freie Säuren, in Form ihrer Salze oder ihrer leicht spaltbaren Ester vorliegen.
• 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.