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Elucidation of the biogenesis of the paraherquamides, malbrancheamides, citrinalins, and brevianamides

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dc.contributor.authorKlas, Kimberly R., author
dc.contributor.authorWilliams, Robert M., advisor
dc.contributor.authorShi, Yian, committee member
dc.contributor.authorChen, Eugene, committee member
dc.contributor.authorCrick, Dean, committee member
dc.date.accessioned2019-09-10T14:35:37Z
dc.date.available2019-09-10T14:35:37Z
dc.date.issued2019
dc.description.abstractVarious fungi of the genera Aspergillus, Penicillium and Malbranchea produce prenylated indole alkaloids that possess a bicyclo[2.2.2]diazaoctane ring system and a variety of biological activities such as insecticidal, cytotoxic, anthelmintic, and antibacterial properties. After the discovery of distinct enantiomers of the natural alkaloids Stephacidin A, Notoamide B and their corresponding diastereomers, from Aspergillus protuberus MF297-2, Aspergillus amoenus NRRL 35660 and Aspergillus taichungensis, the structurally diverse metabolites became of particular biosynthetic interest. The bicyclo[2.2.2]diazaoctane core of the divergent natural metabolites may be enzymatically derived via a putative intramolecular hetero-Diels-Alder cycloaddition. We completed the total synthesis of ZwtP and MeZwtP, unveiling the role of a newly discovered Diels-Alderase. We are also undergoing further synthetic efforts to access other novel natural products, as well as further understand additional unprecedented transformations in nature.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierKlas_colostate_0053A_15518.pdf
dc.identifier.urihttps://hdl.handle.net/10217/197296
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2000-2019
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.subjectcitrinalin
dc.subjectnatural products
dc.subjectZwtP
dc.subjectDiels-Alderase
dc.subjectbrevianamide
dc.subjectprenylated indole alkaloids
dc.titleElucidation of the biogenesis of the paraherquamides, malbrancheamides, citrinalins, and brevianamides
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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