Browsing by Subject "Pyrrolidinones"
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Item Investigation of the Discoipyrroles and Other Marine Bacteria Derived Natural Products(2017-07-17) Colosimo, Dominic Andrew; Bruick, Richard K.; MacMillan, John; Ready, Joseph M.; Nijhawan, DeepakNatural products are a rich source of scientific innovation. These chemical compounds are canonically celebrated as biomedical tools or synthetic chemistry feats. Discovery of new chemical compounds has benefited from the study of natural product biosynthesis, or the methods by which they are constructed. Additionally, these studies have advanced the fields of ecology, industrial chemistry, and protein biophysics. This work will demonstrate how the discoipyrrole family of natural products inspired novel biomedical and biosynthetic discovery. In particular, their biosynthesis features unique mechanisms that are independent of protein catalysts, a growing trend found in natural products. Unrelated to the discoipyrroles, the manipulation of biosynthesis pathways using the methodology known as ribosome engineering will be discussed. This work demonstrates how the discovery and development of bioactive natural products can be enhanced by biosynthetic interrogations.Item Precursor-Directed Identification of Natural Product Scaffolds(2017-04-17) Brumley, David Anderson; MacMillan, JohnThe rapid generation of natural product analogs is a fundamental challenge in both the optimization of medicinal potency and exploration of novel biological activity. Previous work with Streptomyces variabilis has demonstrated that natural products that incorporate non-enzymatic transformation can be exploited for the rapid generation of analogs. Herein we demonstrate a general methodology to use fluorinated or isotopically labeled substrates to identify natural product frameworks prone to non-enzymatic pathways. As proof of principle our precursor directed methodology was used in the study of discoipyrrole A formation, the guided isolation of a novel iminoquinone and the detection of a novel ammosamide analog via incorporation of a carbon-based nucleophile.