Structure and membrane affinity of new amphiphilic siderophores produced by Ochrobactrum sp SP18

Structure and membrane affinity of new amphiphilic siderophores produced by Ochrobactrum sp SP18
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DOI:
10.1007/s00775-006-0112-y
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发表时间:
2006-07-01
影响因子:
3
通讯作者:
Butler, Alison
Butler, Alison
中科院分区:
化学3区
文献类型:
--
作者:
Martin, Jessica D.;Ito, Yusai;Butler, Alison

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沿海α-变形杆菌苍白杆菌属。 SP18 产生一组三种柠檬酸盐衍生的、细胞相关的两亲性铁载体,即 ochrobactins A-C。 ochrobactins 由与两个赖氨酸残基酰胺连接的柠檬酸主链组成。赖氨酸的每个ε-胺被羟基化和酰化,形成两个异羟肟酸部分。每个ochrobactin 的酰化附属物之一是(E)-2-癸烯酸。 ochrobactins A-C 的其他酰化附属物分别是 (E)-2-辛烯酸、辛酸和 (E)-2-癸烯酸。铁赭曲菌素复合物在紫外光下具有光反应性,产生氧化配体,损失 46 个质量单位,但仍可配位 Fe(III)。提出了脱辅基赭菌素、Fe(III) 赭菌素和 Fe(III) 光产物到 1,2-二肉豆蔻酰基-sn-甘油-3-磷酸胆碱囊泡中的相对分配。 ochrobactins 是基于需氧菌素的铁载体的第一个例子,具有两个脂肪酸附属物,在一组具有不同酰基附属物长度的情况下产生。
The coastal alpha-proteobacterium Ochrobactrum sp. SP18 produces a suite of three citrate-derived, cell-associated amphiphilic siderophores, ochrobactins A-C. The ochrobactins are composed of a citric acid backbone amide-linked to two lysine residues. Each epsilon-amine of lysine is hydroxylated and acylated forming two hydroxamic acid moieties. One of the acylated appendages of each ochrobactin is (E)-2-decenoic acid. The other acylated appendages for ochrobactins A-C are (E)-2-octenoic acid, octanoic acid and (E)-2-decenoic acid, respectively. The ferric ochrobactin complexes are photoreactive in UV light, producing an oxidized ligand with loss of 46 mass units that can still coordinate Fe(III). The relative partitioning of the apo-ochrobactins, Fe(III) ochrobactins and Fe(III) photoproducts into 1,2-dimyristoyl-sn-glycero-3-phosphocholine vesicles is presented. The ochrobactins are the first example of aerobactin-based siderophores with two fatty acid appendages produced in a suite with varying acyl appendage lengths.