Farnesyl diphosphate is a biomolecule transformed via a series of carbocation intermediates into the vast number of sesquiterpenes found in nature. Sesquiterpenes are fifteen-carbon secondary metabolites that serve a variety of functions. For example, they aid plants in the protection against predators and in the attraction of pollinators. In addition, they are widely used in the flavors and fragrances industry: some common examples are santalene, which is the characteristic sandalwood scent, and zingiberene, the characteristic flavor of ginger. Scientists estimate there may be 1,000-5,000 sesquiterpene molecules. Each could have 3-5 carbocation intermediates and multiple conformers of these, so in the study of sesquiterpene biosynthesis there could be more than 100,000 isomers or conformers to track! This incredible structural diversity results in a major data organization issue; currently there is no universal way to organize this overwhelming dataset. Further complicating the issue, the majority of datasets regarding sesquiterpene biosynthesis exist within supporting information files or personal research files in a variety of file formats. In the growing movement to make chemical data more FAIR (findable, accessible, interoperable, and reusable), this chaos calls for the formation of a FAIR database of sesquiterpenes. The novel approach described herein uses dihedral angle analysis to uniquely characterize both carbocation pathway intermediates and their resulting natural products. A systematic numbering system, related to but independent of connectivity, has been applied to all data disinterred from the supporting information produced by several research groups. The combination of unique characterization and systematic numbering can facilitate communication amongst different research groups. A more accurate and more useful scientific literature results, as different groups can more easily vet and contextualize new results. Further utility is realized as the database may be mined for new perspectives on the biosynthesis of sesquiterpenes. In summary, the chaos of a vast sesquiterpene database can be brought to order using dihedral angle analysis and a systematic numbering system to develop a searchable database with predictive power, significantly enhancing FAIRness of this dataset.

Bringing order from chaos: FAIR database of sesquiterpenes organized by dihedral angles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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