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Description
The 23-step total synthesis of dolastatin 16, a cyclic depsipeptide of marine origin, is presented. Included are syntheses of nonnatural amino acids dolamethylleuine and dolaphenvaline. The biological activity of the synthetic product differed from naturally isolated dolastatin 16, which may indicate the initial screening identified an inactive compound and the

The 23-step total synthesis of dolastatin 16, a cyclic depsipeptide of marine origin, is presented. Included are syntheses of nonnatural amino acids dolamethylleuine and dolaphenvaline. The biological activity of the synthetic product differed from naturally isolated dolastatin 16, which may indicate the initial screening identified an inactive compound and the active one was not detected initially, or may be a result of the conformational dynamics induced by the proline residues. Additionally, a family of structural analogues to the bacillistatins, another cyclic marine depsipeptide, were synthesized. These were deemed the silstatins. 8 modifications were produced. The alterations aimed to introduce a heteroatomic residue for further derivatization, such as producing an antibody-drug conjugate. This introduction did in general decrease the neoplastic activity of these agents, as expected, but by modulating the lipophilicity of the compound we were able to salvage much of the potency of the bacillistatins while potentially allowing prodrug development.
ContributorsMacdonald, Christian B. (Author) / Pettit, George (Thesis director) / Wang, Xu (Committee member) / Melody, Noeleen (Committee member) / Barrett, The Honors College (Contributor) / Department of Chemistry and Biochemistry (Contributor) / School of Mathematical and Statistical Sciences (Contributor)
Created2015-05
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Description
The discussion of the word “natural” in product marketing and its power to persuade consumers is not often discussed. Research on consumer behavior surrounding “natural” products is compelling due to the current lack of research on the topic and true meaning of the word. Without any legal guidelines for the

The discussion of the word “natural” in product marketing and its power to persuade consumers is not often discussed. Research on consumer behavior surrounding “natural” products is compelling due to the current lack of research on the topic and true meaning of the word. Without any legal guidelines for the marketed use of the word “natural” in the sale of personal care products and cosmetics, consumers’ perceptions of the “naturally” marketed items are subjective. Additionally, brands identify with the word “natural” in different ways, using the word as an ideograph to suggest brand enhancing associations to consumers without legally needing to support these associations.

The following thesis is a creative project that looks at all facets of the “natural” personal care product and cosmetics industry. This includes the origin, history of use, regulations, and consumers’ understanding of the word “natural” in marketing, as well as the identity of the word “natural” as an ideograph. In addition, this project illustrates in-depth analyses of the three major consumer segments of this industry. These analyses uncover each consumer type’s perceived connotations of the word “natural” in personal care product and cosmetics and their characteristics and buying behavior. Lastly, this project features a plan for a digital marketing campaign to showcase this research and incite discussion that raises awareness surrounding the word “natural” in the beauty space.
ContributorsPaulson, Katherine (Author) / Hass, Mark (Thesis director) / Gray, Nancy (Committee member) / Department of Marketing (Contributor) / Barrett, The Honors College (Contributor)
Created2020-12