Structural and Biosynthetic Analysis of the Fabrubactins, Unusual Siderophores from Agrobacterium fabrum Strain C58,ACS Chemical Biology

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Structural and Biosynthetic Analysis of the Fabrubactins, Unusual Siderophores from Agrobacterium fabrum Strain C58
ACS Chemical Biology ( IF 3.5 ) Pub Date : 2020-12-29 , DOI: 10.1021/acschembio.0c00809
Vladimir Vinnik _{1,

2} , Fan Zhang ₃ , Hyunjun Park _{1,

4} , Taylor B Cook ₅ , Kurt Throckmorton ₁ , Brian F Pfleger ₅ , Tim S Bugni ₃ , Michael G Thomas ₁

Affiliation

Siderophores are iron-chelating molecules produced by microorganisms and plants to acquire exogenous iron. Siderophore biosynthetic enzymology often produces elaborate and unique molecules through unusual reactions to enable specific recognition by the producing organisms. Herein, we report the structure of two siderophore analogs from Agrobacterium fabrum strain C58, which we named fabrubactin (FBN) A and FBN B. Additionally, we characterized the substrate specificities of the NRPS and PKS components. The structures suggest unique Favorskii-like rearrangements of the molecular backbone that we propose are catalyzed by the flavin-dependent monooxygenase, FbnE. FBN A and B contain a 1,1-dimethyl-3-amino-1,2,3,4-tetrahydro-7,8-dihydroxy-quinolin (Dmaq) moiety previously seen only in the anachelin cyanobacterial siderophores. We provide evidence that Dmaq is derived from l-DOPA and propose a mechanism for the formation of the mature Dmaq moiety. Our bioinformatic analyses suggest that FBN A and B and the anachelins belong to a large and diverse siderophore family widespread throughout the Rhizobium/Agrobacterium group, α-proteobacteria, and cyanobacteria.

中文翻译：

Fabrubactins 的结构和生物合成分析，来自农杆菌 C58 菌株的异常铁载体

铁载体是微生物和植物为获取外源铁而产生的铁螯合分子。铁载体生物合成酶学通常通过不寻常的反应产生精细且独特的分子，以使生产生物能够特异性识别。在此，我们报告了来自农杆菌的两种铁载体类似物的结构菌株 C58，我们将其命名为 fabrubactin (FBN) A 和 FBN B。此外，我们表征了 NRPS 和 PKS 组分的底物特异性。这些结构表明我们提出的分子骨架的独特 Favorskii 样重排是由黄素依赖性单加氧酶 FbnE 催化的。FBN A 和 B 含有 1,1-二甲基-3-氨基-1,2,3,4-四氢-7,8-二羟基喹啉 (Dmaq) 部分，以前仅在 anachelin 蓝藻铁载体中可见。我们提供了 Dmaq 源自l- DOPA 的证据，并提出了成熟 Dmaq 部分形成的机制。我们的生物信息学分析表明，FBN A 和 B 以及 anachelins 属于广泛存在于根瘤菌/农杆菌中的一个庞大而多样的铁载体家族 组，α-变形菌和蓝细菌。

更新日期：2021-01-15

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