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To develop strategies for the successful incorporation of radiocarbon into ergopeptine alkaloids present in Neotyphodium-infected Tall Fescue. Specific objectives are to incorporate radiocarbon into the tricyclic peptide portion ergovaline, the predominant ergopeptidine alkaloid present in endophyte-infected Tall Fescue.
Chemical synthesis of radiolabeled ergopeptidine alkaloids will be accomplished through the stepwise synthesis of component portions of the molecule. Namely, radiolabeled precursors, such as [14C] proline or [14C] valine, will be purchased and incorporated into the tricyclic peptidine portion of the molecule using chemical techniques developed during preliminary studies with nonradioactive materials. The tricyclic peptide portion of the molecule will be coupled to lysergic acid using standard coupling techniques, which have been previously validated with nonradioactive materials. Incorporation of [14C] precursors into the lysergic acid portion of ergopeptidine precursors through chemical syntheses or through culture techniques followed by chemical syntheses may be pursued depending upon results obtained from metabolism studies performed with chemically synthesized [14C] ergovaline.