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Significance Domoic acid is a neurotoxin produced by marine algae that readily bioaccumulates in shellfish with significant impacts for both human and animal lives. The first committed step of domoic acid biosynthesis is theN -prenylation ofl -glutamic acid catalyzed by DabA. By solving the crystal structure of DabA, we demonstrate that DabA repurposed the phylogenetically ubiquitous terpene cyclase fold to catalyze a rarer reaction,N -prenylation of a primary amine. These structural insights enabled the rational engineering of twoN -prenyltransferases to accept alternative prenyl donors. These results expand our understanding of the reaction scope catalyzed by terpene cyclase folds and will inform future domoic acid environmental monitoring efforts.

Algal neurotoxin biosynthesis repurposes the terpene cyclase structural fold into an N -prenyltransferase