Abstract by Blake Christensen
Chemistry and Biochemistry
Synthesis of Complex Amino Acids in Yaku\'amide A
Yaku’amide A (YA) is a scarce peptide that is toxic against P388 murine leukemia cells, and showed a novel mode of action when being tested against a JFCR-39 panel of cancer cell lines. YA contains β-hydroxy amino acids β-OH Val and β-OH Ile and the dehydroamino acids (∆AA) - E and Z-dehydro(Ile). Inoue and coworkers achieved the total synthesis of YA in 86 steps. Challenges in synthesizing β-OH AAs and ∆AAs contributed to the great length of Inoue’s route. We are developing new innovative methods for synthesizing these AAs in order to achieve a concise synthesis of YA, which will enable studies of its mode of action. My part in this project is to build the key β-OH AAs and ∆AAs using a newly discovered method. By using commercially available starting materials our synthesis will be simple and useful for future exploration of YA’s biomedical and molecular targets.