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Abstract by Blake Christensen

Personal Infomation


Presenter's Name

Blake Christensen

Degree Level

Undergraduate

Abstract Infomation


Department

Chemistry and Biochemistry

Faculty Advisor

Steven Castle

Title

Synthesis of Complex Amino Acids in Yaku'amide A

Abstract

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.