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铜绿假单胞菌素的结构与生物合成组装,一种来自生物塑料生产菌恶臭假单胞菌 H16 的光反应性铁载体。

Structure and biosynthetic assembly of cupriachelin, a photoreactive siderophore from the bioplastic producer Cupriavidus necator H16.

机构信息

Junior Research Group Secondary Metabolism of Predatory Bacteria, Hans-Knöll-Institute, Beutenbergstrasse 11a, 07745 Jena, Germany.

出版信息

J Am Chem Soc. 2012 Mar 21;134(11):5415-22. doi: 10.1021/ja300620z. Epub 2012 Mar 13.

DOI:10.1021/ja300620z
PMID:22381697
Abstract

The bacterium Cupriavidus necator H16 produces a family of linear lipopeptides when grown under low iron conditions. The structural composition of these molecules, exemplified by the main metabolite cupriachelin, is reminiscent of siderophores that are excreted by marine bacteria. Comparable to marine siderophores, the ferric form of cupriachelin exhibits photoreactive properties. Exposure to UV light induces an oxidation of its peptidic backbone and a concomitant reduction of the coordinated Fe(III). Here, we report the genomics-inspired isolation and structural characterization of cupriachelin as well as its encoding gene cluster, which was identified by insertional mutagenesis. Based upon the functional characterization of adenylation domain specificity, a model for cupriachelin biosynthesis is proposed.

摘要

当铜绿假单胞菌 H16 在低铁条件下生长时,会产生一系列线性脂肽。这些分子的结构组成,以主要代谢产物铜铁灵为例,让人联想到海洋细菌分泌的铁载体。与海洋铁载体类似,铜铁灵的三价铁形式表现出光反应性。暴露在紫外线下会诱导其肽骨架氧化,并伴随配位的 Fe(III)还原。在这里,我们报告了基于基因组学的铜铁灵的分离和结构表征,以及通过插入诱变鉴定的其编码基因簇。基于腺嘌呤转移酶结构域特异性的功能表征,提出了铜铁灵生物合成的模型。

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