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            <title xml:lang="en">Reprogramming Escherichia coli for the production of prenylated indole diketopiperazine alkaloids</title>
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                <forename type="first">Pavlina</forename>
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            <funder>This work was supported by the French Alternative Energies and Atomic Energy Commission (CEA), the French National Centre for Scientific Research (CNRS), the Sorbonne University and the French National Research Agency (grant ANR-16-CE29-0026).</funder>
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                <title xml:lang="en">Reprogramming Escherichia coli for the production of prenylated indole diketopiperazine alkaloids</title>
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                <title level="j">Scientific Reports</title>
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              <p>Abstract Prenylated indole diketopiperazine (DKP) alkaloids are important bioactive molecules or their precursors. In the context of synthetic biology, efficient means for their biological production would increase their chemical diversification and the discovery of novel bioactive compounds. Here, we prove the suitability of the Escherichia coli chassis for the production of prenylated indole DKP alkaloids. We used enzyme combinations not found in nature by co-expressing bacterial cyclodipeptide synthases (CDPSs) that assemble the DKP ring and fungal prenyltransferases (PTs) that transfer the allylic moiety from the dimethylallyl diphosphate (DMAPP) to the indole ring of tryptophanyl-containing cyclodipeptides. Of the 11 tested combinations, seven resulted in the production of eight different prenylated indole DKP alkaloids as determined by LC-MS/MS and NMR characterization. Two were previously undescribed. Engineering E. coli by introducing a hybrid mevalonate pathway for increasing intracellular DMAPP levels improved prenylated indole DKP alkaloid production. Purified product yields of 2–26 mg/L per culture were obtained from culture supernatants. Our study paves the way for the bioproduction of novel prenylated indole DKP alkaloids in a tractable chassis that can exploit the cyclodipeptide diversity achievable with CDPSs and the numerous described PT activities.</p>
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              <org type="consortium">We thank Dr Taek Soon Lee and Melanya Gudzeva from the Lawrence Berkeley National Laboratory for providing us with plasmids pJBEI-3085 and pJBEI-3122.</org>
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