Abstract

Yaku'amide A shows a unique inhibitory profile against a series of 39 human cancer cell lines (JFCR39). In our efforts to synthesize yaku'amide A, we have optimized our regioselective base-free aminohydroxylation method with a series of nitrogen sources, developed a chiral reagent-mediated aminohydroxylation strategy and chemoselective deprotections of the resulting aminohydroxylation product, and explored a stereospecific E2 dehydration and O-N acyl transfer sequence. In addition, we have prepared the right-hand tetrapeptide and the NTA subunit. For our bulky α,β-dehydroamino acids project, we have developed strategies to incorporate α,β-dehydroamino acids such as ΔVal and ΔEnv into small synthetic peptides via Solid Phase Peptide Synthesis (SPPS). We have also prepared two analogues of a monomeric helical peptide with 13 residues.

Degree

PhD

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

Rights

http://lib.byu.edu/about/copyright/

Date Submitted

2016-07-01

Document Type

Dissertation

Handle

http://hdl.lib.byu.edu/1877/etd8883

Keywords

yaku'amide A, inhibitory profile, chiral reagent-mediated aminohydroxylation, chemoselective deprotections, stereospecific E2 dehydration, right-hand tetrapeptide, NTA, bulky α, β-dehydroamino acids, ΔVal and ΔEnv, SPPS, analogues

Included in

Chemistry Commons

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