A biocompatible Lossen rearrangement in Escherichia coli

IF 20.2 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Nature chemistry Pub Date : 2025-06-23 DOI:10.1038/s41557-025-01845-5

Nick W. Johnson, Marcos Valenzuela-Ortega, Thomas W. Thorpe, Yuta Era, Annemette Kjeldsen, Keith Mulholland, Stephen Wallace

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引用次数: 0

Abstract

Nature has evolved an exquisite yet limited set of chemical reactions that underpin the function of all living organisms. By contrast, the field of synthetic organic chemistry can access reactivity not observed in nature, and integration of these abiotic reactions within living systems offers an elegant solution to the sustainable synthesis of many industrial chemicals from renewable feedstocks. Here we report a biocompatible Lossen rearrangement that is catalysed by phosphate in the bacterium Escherichia coli for the transformation of activated acyl hydroxamates to primary amine-containing metabolites in living cells. Through auxotroph rescue, we demonstrate how this new-to-nature reaction can be used to control microbial growth and chemistry by generating the essential metabolite para-aminobenzoic acid. The Lossen rearrangement substrate can also be synthesized from polyethylene terephthalate and applied to whole-cell biocatalytic reactions and fermentations generating industrial small molecules (including the drug paracetamol), paving the way for a general strategy to bioremediate and upcycle plastic waste in native and engineered biological systems.

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大肠杆菌中的生物相容性Lossen重排

大自然已经进化出一套精致而有限的化学反应，支撑着所有生物的功能。相比之下，合成有机化学领域可以获得在自然界中观察不到的反应性，并且将这些非生物反应整合到生命系统中，为从可再生原料中可持续合成许多工业化学品提供了一个优雅的解决方案。在这里，我们报道了一种生物相容性的Lossen重排，这种重排是由大肠杆菌中的磷酸盐催化的，用于将活化的酰基羟酸盐转化为活细胞中含有初级胺的代谢物。通过营养不良救援，我们展示了这种新的自然反应如何通过产生必需代谢物对氨基苯甲酸来控制微生物生长和化学反应。Lossen重排底物也可以由聚对苯二甲酸乙二醇酯合成，并应用于全细胞生物催化反应和发酵，产生工业小分子（包括药物扑热扑痛），为在天然和工程生物系统中进行生物修复和塑料废物升级循环的一般策略铺平了道路。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Nature chemistry 化学-化学综合

CiteScore

29.60

自引率

1.40%

发文量

226

审稿时长

1.7 months

期刊介绍： Nature Chemistry is a monthly journal that publishes groundbreaking and significant research in all areas of chemistry. It covers traditional subjects such as analytical, inorganic, organic, and physical chemistry, as well as a wide range of other topics including catalysis, computational and theoretical chemistry, and environmental chemistry. The journal also features interdisciplinary research at the interface of chemistry with biology, materials science, nanotechnology, and physics. Manuscripts detailing such multidisciplinary work are encouraged, as long as the central theme pertains to chemistry. Aside from primary research, Nature Chemistry publishes review articles, news and views, research highlights from other journals, commentaries, book reviews, correspondence, and analysis of the broader chemical landscape. It also addresses crucial issues related to education, funding, policy, intellectual property, and the societal impact of chemistry. Nature Chemistry is dedicated to ensuring the highest standards of original research through a fair and rigorous review process. It offers authors maximum visibility for their papers, access to a broad readership, exceptional copy editing and production standards, rapid publication, and independence from academic societies and other vested interests. Overall, Nature Chemistry aims to be the authoritative voice of the global chemical community.