Biocompatible 1,2-carbonyl rearrangements in living E. coli Nick W. Johnson 1 , Keith Mulholland 2 and Stephen Wallace* 1 1 University of Edinburgh, UK, 2 AstraZeneca, UK Engineered microorganisms are increasingly used in industry as a sustainable source of small molecules. However, native biosynthetic pathways are limited to the generation of molecules already occurring in Nature. One method to introduce this non-native reactivity into a living organism is through the use of abiotic catalysis. By developing and interfacing non-enzymatic biocompatible reactions with microbial metabolism, this could increase the synthetic opportunities provided by biotechnology for the production of value-added compounds 1 . 1,2-carbonyl rearrangements are examples of important functional group transformations not accessed in biology. To address this, we have demonstrated an abiotic 1,2-carbonyl rearrangement in the presence of living Escherichia coli cells - specifically, we observed cell growth of an auxotrophic strain only in the presence of our substrate. Reactivity occurred in M9 growth media, indicating that product formation was dependent on the presence of a biocompatible catalyst. Furthermore, this aqueous rearrangement can interface with enzymatic processes and can be adapted to a range of substrates and products, highlighting how this transformation is applicable to larger, previously inaccessible, biosynthetic pathways.
References 1. Sadler, J.C., Dennis, J.A., Johnson, N.W., Wallace, S., Interfacing non-enzymatic catalysis with living microorganisms, RSC Chem. Biol. , 2021, 2 , 1073-1083.
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