N-(15,27-diacetamido-10,22,34-trimethyl-7,19,31-trioxido-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-trien-3-yl)acetamide;iron(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: N-(15,27-diacetamido-10,22,34-trimethyl-7,19,31-trioxido-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-trien-3-yl)acetamide;iron(3+)
• 化学式: C₃₉H₅₇N₆O₁₅*Fe
• 分子量: 905.76
• InChiKey: UIVTVLVVAXJPKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  61
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  296
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  铁粉 、 N',N'',N'''-triacetylfusarinine C 在 potassium chloride 作用下， 以 水 为溶剂， 生成 N-(15,27-diacetamido-10,22,34-trimethyl-7,19,31-trioxido-2,8,14,20,26,32-hexaoxo-1,13,25-trioxa-7,19,31-triazacyclohexatriaconta-9,21,33-trien-3-yl)acetamide;iron(3+)
  参考文献：
  名称：

  Mn(II)/Mn(III) and Fe(III) binding capability of two Aspergillus fumigatus siderophores, desferricrocin and N′, N″, N‴-triacetylfusarinine C

  摘要：

  Manganese(II) and manganese(III) complexes of the exocyclic desferricrocin (H3DFCR) and endocyclic triacetylfusarinine C (H(3)TAF) in solution have been studied by using pH-potentiometry, UV-Vis spectrophotometry, relaxometry and cyclic voltammetry. A comparison between the present results and the corresponding ones for the open-chain analogues, desferrioxamine B (DFB) and desferricoprogen (DFC), shows (i) The dissociation processes of H3DFCR occur in the expected pH-range (pH 7-10.5), but hydrogen bonding is assumed to be responsible for a quite low proton dissociation constant (pK = 4.18) of H3TAF and also an unusually high one (10.59). (ii) Moderate stability complexes with 1:1 Mn(II) to ligand ratio are formed with all four siderophores. (iii) The coordination of the three hydroxamates of a siderophore takes place in stepwise processes, except the case of desferricrocin, with which, large-extent overlapping of the processes occurs. (iv) Out of the four tris-chelated [ML] type complexes, the complex of DFCR is the most compact, as it is indicated by the relaxivity values. (v) Following the stoichiometric oxidation of the Mn(II)-siderophore complexes at pH >= 9, tris-chelated Mn(III) complexes are formed. To make a comparison between the stability of the Mn(III) and the corresponding Fe(III) complexes of DFCR and TAF, the determination of the stability of the Fe(III) complexes under our condition has also been performed, by using UV-Vis spectrophotometry. Comparable stability of the corresponding complexes was found. (vi) Correlation study of the stability constants resulted in estimation of the constant of the Mn(III) monohydroxo complex, for which there was no data in the literature under our conditions. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.06.005

文献信息

• Mn(II)/Mn(III) and Fe(III) binding capability of two Aspergillus fumigatus siderophores, desferricrocin and N′, N″, N‴-triacetylfusarinine C
  作者：Etelka Farkas、Orsolya Szabó、Péter L. Parajdi-Losonczi、György Balla、István Pócsi

  DOI：10.1016/j.jinorgbio.2014.06.005

  日期：2014.10

  Manganese(II) and manganese(III) complexes of the exocyclic desferricrocin (H3DFCR) and endocyclic triacetylfusarinine C (H(3)TAF) in solution have been studied by using pH-potentiometry, UV-Vis spectrophotometry, relaxometry and cyclic voltammetry. A comparison between the present results and the corresponding ones for the open-chain analogues, desferrioxamine B (DFB) and desferricoprogen (DFC), shows (i) The dissociation processes of H3DFCR occur in the expected pH-range (pH 7-10.5), but hydrogen bonding is assumed to be responsible for a quite low proton dissociation constant (pK = 4.18) of H3TAF and also an unusually high one (10.59). (ii) Moderate stability complexes with 1:1 Mn(II) to ligand ratio are formed with all four siderophores. (iii) The coordination of the three hydroxamates of a siderophore takes place in stepwise processes, except the case of desferricrocin, with which, large-extent overlapping of the processes occurs. (iv) Out of the four tris-chelated [ML] type complexes, the complex of DFCR is the most compact, as it is indicated by the relaxivity values. (v) Following the stoichiometric oxidation of the Mn(II)-siderophore complexes at pH >= 9, tris-chelated Mn(III) complexes are formed. To make a comparison between the stability of the Mn(III) and the corresponding Fe(III) complexes of DFCR and TAF, the determination of the stability of the Fe(III) complexes under our condition has also been performed, by using UV-Vis spectrophotometry. Comparable stability of the corresponding complexes was found. (vi) Correlation study of the stability constants resulted in estimation of the constant of the Mn(III) monohydroxo complex, for which there was no data in the literature under our conditions. (C) 2014 Elsevier Inc. All rights reserved.