Asperparaline A: biosynthetic studies and synthetic efforts
| dc.contributor.author | Gray, Chandele Ramsey, author | |
| dc.contributor.author | Williams, Robert M., advisor | |
| dc.contributor.author | Kennan, Alan, committee member | |
| dc.contributor.author | Szamel, Grzegorz, committee member | |
| dc.contributor.author | Parkinson, Bruce, committee member | |
| dc.contributor.author | Brennan, Patrick, committee member | |
| dc.date.accessioned | 2022-11-28T17:46:45Z | |
| dc.date.available | 2022-11-28T17:46:45Z | |
| dc.date.issued | 2008 | |
| dc.description.abstract | Asperparaline A, a fungal metabolite isolated from Aspergillus japonicus, is of interest due to anthelmintic activity and structural similarities to the paraherquamides and brevianamides owing to the presence of bicyclo [2.2.2] diazaoctane core proposed to be derived from a biosynthetic [4+2] cycloaddition. This communication details two aspects of research regarding asperparaline A. The first goal involves the elucidation of asperparaline A as being biosynthetically composed of dimethylallylpyrophosphate and the amino acids, tryptophan and L-isoleucine, analogous to the paraherquamides. The second goal addresses the desire to develop synthetic methodology amenable to the introduction of isotopic labels for further biosynthetic studies. The proposed retrosyntheses envision the spiro-succinimide ring of asperparaline A being introduced by the photooxidation of a suitably oxidized pyrrole ring. Synthetic approaches toward asperparaline A presented include peptide coupling of β-methylproline with a prenylated pyrolylalanine, and Horner-Wadsworth-Emmons olefination of a diketopiperazine phosphonate with various aldehydes designed to allow for late stage pyrrole synthesis. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235852 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991009862799703361 | |
| dc.relation | QR84.G738 2008 | |
| dc.relation.ispartof | 2000-2019 | |
| dc.rights | Copyright 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.subject | Fungal metabolites | |
| dc.subject | Anthelmintics | |
| dc.subject | Biosynthesis | |
| dc.subject | Indole alkaloids | |
| dc.title | Asperparaline A: biosynthetic studies and synthetic efforts | |
| dc.type | Text | |
| dcterms.rights.dpla | This 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.discipline | Chemistry | |
| thesis.degree.grantor | Colorado State University | |
| thesis.degree.level | Doctoral | |
| thesis.degree.name | Doctor of Philosophy (Ph.D.) |