desferrioxamine P₁ | 129693-94-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: desferrioxamine P₁
• 英文别名: Desferrioxamine P1；1,12,23-trihydroxy-1,4,7,12,18,23,29-heptazacyclotritriacontane-3,8,11,19,22,30,33-heptone
• CAS: 129693-94-3
• 化学式: C₂₆H₄₅N₇O₁₀
• 分子量: 615.684
• InChiKey: XDOZZFLMQKAFFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  43
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  238
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-(2-Aminoethyl)glycinamide 生成 desferrioxamine P₁
  参考文献：
  名称：

  Solution thermodynamics of the ferric complexes of new desferrioxamine siderophores obtained by directed fermentation

  摘要：

  Thirteen new desferrioxamine-type siderophores, designated X1-X6, Et1-Et3, Te1-Te3, and P1, were obtained from cultures of Streptomyces olivaceus Tu 2718 by supplementing the production medium with ornithine or 1,4-diaminobutane, 1,6-diaminohexane, bis(2-aminoethyl) ether, S-(2-aminoethyl)cysteine, and N-glycylethylenediamine. The stability constants of the ferric complexes of the trihydroxamate ligands, X1-X4, Et1-Et3, and Te1-Te3, were determined by EDTA competition reactions and are in the range log beta-110 = 29.7-31.8 (beta-110 = [FeL]/([Fe3+] [L3-], 25-degrees-C, 0.1 M KNO3). The stability of the complexes decreases monotonically as the structure of the ligand differs from that of desferrioxamine E (beta-110 = 32.21, 25-degrees-C, 0.1 M KNO3), the main siderophore of S. olivaceus Tu 2718 under natural growth conditions. The dihydroxamic acid desferrioxamine X5 forms two types of ferric complexes, depending on pH. The predominant species above pH 6.4 is a dimer of formulation Fe2L3, Which dissociates into a monomeric cation, FeL+, at lower pH. The stability constants of these two species determined by spectrophotometric titration are log beta-230 = 55.35 and log beta-110 = 19.18 (25-degrees-C, 0.1 M KNO3). The relative effectiveness of the new ferrioxamines as mediators of iron uptake via the hydroxamate ferric ion transport system of Staphylococcus aureus DSM 799 differs widely, however, without correlating with the complex stability.

  DOI：

  10.1021/ja00032a043

文献信息

• FIEDLER, H. -P.;MEIWES, J.;WERNER, I.;KONETSCHNY-RAPP, S.;JUNG, G., J. CHROMATOGR., 513,(1990) C. 255-262
  作者：FIEDLER, H. -P.、MEIWES, J.、WERNER, I.、KONETSCHNY-RAPP, S.、JUNG, G.

  DOI：——

  日期：——
• Solution thermodynamics of the ferric complexes of new desferrioxamine siderophores obtained by directed fermentation
  作者：Silvia Konetschny-Rapp、Guenther Jung、Kenneth N. Raymond、Johannes Meiwes、Hans Zaehner

  DOI：10.1021/ja00032a043

  日期：1992.3

  Thirteen new desferrioxamine-type siderophores, designated X1-X6, Et1-Et3, Te1-Te3, and P1, were obtained from cultures of Streptomyces olivaceus Tu 2718 by supplementing the production medium with ornithine or 1,4-diaminobutane, 1,6-diaminohexane, bis(2-aminoethyl) ether, S-(2-aminoethyl)cysteine, and N-glycylethylenediamine. The stability constants of the ferric complexes of the trihydroxamate ligands, X1-X4, Et1-Et3, and Te1-Te3, were determined by EDTA competition reactions and are in the range log beta-110 = 29.7-31.8 (beta-110 = [FeL]/([Fe3+] [L3-], 25-degrees-C, 0.1 M KNO3). The stability of the complexes decreases monotonically as the structure of the ligand differs from that of desferrioxamine E (beta-110 = 32.21, 25-degrees-C, 0.1 M KNO3), the main siderophore of S. olivaceus Tu 2718 under natural growth conditions. The dihydroxamic acid desferrioxamine X5 forms two types of ferric complexes, depending on pH. The predominant species above pH 6.4 is a dimer of formulation Fe2L3, Which dissociates into a monomeric cation, FeL+, at lower pH. The stability constants of these two species determined by spectrophotometric titration are log beta-230 = 55.35 and log beta-110 = 19.18 (25-degrees-C, 0.1 M KNO3). The relative effectiveness of the new ferrioxamines as mediators of iron uptake via the hydroxamate ferric ion transport system of Staphylococcus aureus DSM 799 differs widely, however, without correlating with the complex stability.