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Investigating biosynthetic pathways of the Aspergillus genus through biomimetic total synthesis of secondary metabolites

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dc.contributor.authorBenson, Brooke, author
dc.contributor.authorWilliams, Robert M., advisor
dc.contributor.authorKennan, Alan J., advisor
dc.contributor.authorPaton, Robert, committee member
dc.contributor.authorCrans, Debbie, committee member
dc.contributor.authorCrick, Dean, committee member
dc.date.accessioned2022-05-30T10:22:23Z
dc.date.available2022-05-30T10:22:23Z
dc.date.issued2022
dc.description.abstractThe prenylated indole alkaloids are a class of secondary metabolites containing a unique bicyclo[2.2.2]diazaoctane core and a wide range of biological activity. This complex structure has prompted extensive investigation into the biochemical synthesis of these compounds. Currently, three disparate biochemical strategies are known to be used by producing fungi to construct the bicyclic core: (1) NADPH-dependent bifunctional reductase/Diels-Alderase-mediation in formation of the monooxopiperazines; (2) brevianamide assembly through cofactor-independent pinacolase resulting in spontaneous intramolecular Diels-Alder (IMDA) generation of the bicyclo[2.2.2]diazaoctane core; (3) Diels-Alderase mediated enantiodivergent generation of the dioxopiperazines via cytochrome P450 oxidation to achiral azadienes and successive enzyme-mediated stereoselective IMDA reaction. This work aimed to employ biomimetic total synthesis to aid in elucidation of the biosynthetic pathways in the Aspergillus genus, which utilizes the third strategy. This author reports the first total syntheses of 6-epi-Notoamides T10-12 and Notoamide T2, as well as an improved total synthesis of 6-epi-Notoamide T. Also reported are synthetic efforts towards 6-epi-Notoamide T9, Notoamide TI, and Citrinalin C.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierBenson_colostate_0053A_17011.pdf
dc.identifier.urihttps://hdl.handle.net/10217/235263
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2020-
dc.rightsCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.
dc.subjectbiomimetic
dc.subjectnatural products
dc.subjectsynthesis
dc.subjectbiosynthesis
dc.subject6-epi-Notoamide
dc.subjectNotoamide
dc.titleInvestigating biosynthetic pathways of the Aspergillus genus through biomimetic total synthesis of secondary metabolites
dc.typeText
dcterms.rights.dplaThis Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

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