Theonellamide is a bicyclic peptide isolated from a marine sponge, which shows interesting biological activity. It contains several unnatural amino acids, among which are (2S,3R)-3-hydroxyasparagine (L-erythro-β-hydroxyasparagine) (β-OHAsn) and τ-L-histindino-D-alanine (τ-HAL). Although there were previous synthetic efforts toward each of these unnatural amino acids, the efforts were not ideal due to expensive starting material, time-consuming steps, and poor regioselectivity. The presented work demonstrates an inexpensive, enantioselective synthesis of β-OHAsn, which can be completed in a matter of weeks, as well as several attempts at a novel regiospecific approach toward τ-HAL, including work on a model study.
College and Department
Physical and Mathematical Sciences; Chemistry and Biochemistry
BYU ScholarsArchive Citation
Bettale, Jennifer Dawn, "Progress Toward Theonellamide F" (2011). All Theses and Dissertations. 3022.
Theonellamide, bicyclic peptide, β-OHAsn, τ-HAL