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Scalable biosynthesis of the seaweed neurochemical, kainic acid

TitleScalable biosynthesis of the seaweed neurochemical, kainic acid
Publication TypeJournal Article
Year of Publication2019
AuthorsChekan J.R, McKinnie S.MK, Moore M.L, Poplawski S.G, Michael T.P, Moore BS
Volume58
Pagination8454-8457
Date Published2019/06
Type of ArticleArticle
ISBN Number1433-7851
Accession NumberWOS:000476608700028
Keywordsbiosynthesis; Biotransformation; chemistry; cloning; gene clusters; genome; kainic acid; model; natural product; red algae
Abstract

Kainic acid, the flagship member of the kainoid family of natural neurochemicals, is a widely used neuropharmacological agent that helped unravel the key role of ionotropic glutamate receptors, including the kainate receptor, in the central nervous system. Worldwide shortages of this seaweed natural product in the year 2000 prompted numerous chemical syntheses, including scalable preparations with as few as six-steps. Herein we report the discovery and characterization of the concise two-enzyme biosynthetic pathway to kainic acid from l-glutamic acid and dimethylallyl pyrophosphate in red macroalgae and show that the biosynthetic genes are co-clustered in genomes of Digenea simplex and Palmaria palmata. Moreover, we applied a key biosynthetic alpha-ketoglutarate-dependent dioxygenase enzyme in a biotransformation methodology to efficiently construct kainic acid on the gram scale. This study establishes both the feasibility of mining seaweed genomes for their biotechnological prowess.

DOI10.1002/anie.201902910
Student Publication: 
No
Research Topics: