Enzymatic tailoring of ornithine in the biosynthesis of the Rhizobium cyclic trihydroxamate siderophore vicibactin.
Enzymatic tailoring of ornithine in the biosynthesis of the Rhizobium cyclic trihydroxamate siderophore vicibactin.
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DOI：
10.1021/ja9056008
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发表时间：
2009-10-28
影响因子：
15
通讯作者：
Sattely, Elizabeth S.
中科院分区：
文献类型：
--
作者：
Heemstra, John R., Jr.;Walsh, Christopher T.;Sattely, Elizabeth S.
为了获得铁，固氮共生细菌根瘤菌产生环状三异羟肟酸铁载体vicibactin，含有30元三内酯支架。在这里，我们报告的过量生产和纯化的六种蛋白质VbsACGOLS在细菌宿主大肠杆菌和重建的vicibactin的生物合成的初级代谢产物。黄素蛋白VbsO作为途径起始的L-鸟氨酸N5-羟化酶，随后是VbsA，其将（R）-3-羟基丁酰基-从CoA硫酯转移至N5-羟基鸟氨酸以产生N5-（（R）-3-羟基丁酰基）-N5-羟基-L-鸟氨酸。VbsL是作用于10个原子单体单元的C2的PLP依赖性差向异构酶。VbsS是一种非核糖体肽合成酶独立模块，然后在环三聚化成vicibactin支架的过程中激活N5-（（R）-3-羟基丁酰基）-N5-羟基-D-鸟氨酸作为AMP酸酐。最后一步，脱乙酰基-D-vicibactin的C2氨基的三乙酰化为成熟的铁载体vicibactin由VbsC使用三个乙酰辅酶A分子分布催化。
To acquire iron, the N2-fixing, symbiotic bacterium Rhizobium sp. produce the cyclic tri-hydroxamate siderophore vicibactin, containing a 30-membered tri-lactone scaffold. Herein we report the overproduction and purification of the six proteins VbsACGOLS in the bacterial host Escherichia coli and the reconstitution of the biosynthesis of vicibactin from primary metabolites. The flavoprotein VbsO acts as a pathway-initiating L-ornithine N5-hydroxylase, followed by VbsA which transfers (R)-3-hydroxybutyryl- from the CoA thioester to N5-hydroxyornithine to yield N5-((R)-3-hydroxybutyryl)-N5-hydroxy-L-ornithine. VbsL is a PLP-dependent epimerase acting at C2 of the 10 atom monomer unit. VbsS, a nonribosomal peptide synthetase free standing module, then activates N5-((R)-3-hydroxybutyryl)-N5-hydroxy-D-ornithine as the AMP anhydride on the way to cyclotrimerization to the vicibactin scaffold. The last step, tris-acetylation of the C2 amino group of desacetyl-D-vicibactin to the mature siderophore vicibactin is catalyzed distributively by VbsC, using three molecules of acetyl-CoA.
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