Nerolidyl diphosphate is a biomolecule that is transformed into a wide range of secondary metabolites exhibiting a remarkable diversity of molecular structures. These secondary metabolites follow the biogenetic isoprene rule and contain 15 carbons so they are classified as sesquiterpenes. Various organisms generate sesquiterpenes to serve a variety of biological functions. Well-known derivatives of nerolidyl diphosphate spotlight the importance of these molecules in the flavors and fragrances industry: bergamotene, from oil of bergamot, gives Earl Grey tea is distinctive flavor; santalene, found in sandalwood oil, is a popular fragrance; and zingiberene provides the characteristic flavor of ginger. The diversity of sesquiterpene structures has fascinated scientists for many years. This diversity, however, provides a challenge: there are hundreds of constitutional isomers and even more proposed biosynthetic intermediates, each structure potentially displaying multiple conformational isomers. In addition, the literature has several standards for nomenclature and atom numbering along with erroneous structures. The work presented in this poster seeks to bring order from this chaos by establishing a systematic, searchable database of sesquiterpene structures organized by their conformation (as opposed to their connectivity). Building on key conformational markers, preliminary work suggests this database has capacity for more than 1 million unique entries. This database will include both known sesquiterpenes and proposed carbocations intermediates derived from nerolidyl diphosphate. The decision to include both constitutional and conformational isomers not only fills a void in existing databases, it also facilitates the correlation of modern and historical datasets. An addition benefit is that the database complements its descriptive ability with predictive power. Preliminary data-mining has suggested new approaches to the analysis of structure-function relationships in the enzyme-substrate complex and to identify potential errors in the literature. Long-term potential for this database includes its application to sesquiterpenoids (sesquiterpenes containing atoms in addition to carbon and hydrogen, most typically oxygen) as well as inclusion of other terpenes and terpenoids, those with fewer or more than 15 carbons, further addressing a void in existing chemical databases.

Organizing the pathways and products of nerolidyl diphosphate into a searchable database

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.