dc.contributor.advisor | Romo, Daniel | |
dc.creator | Lee, Chang Suk | |
dc.date.accessioned | 2011-08-08T22:47:43Z | |
dc.date.accessioned | 2011-08-09T01:33:30Z | |
dc.date.available | 2011-08-08T22:47:43Z | |
dc.date.available | 2011-08-09T01:33:30Z | |
dc.date.created | 2010-05 | |
dc.date.issued | 2011-08-08 | |
dc.date.submitted | May 2010 | |
dc.identifier.uri | https://hdl.handle.net/1969.1/ETD-TAMU-2010-05-7768 | |
dc.description.abstract | Contamination of seafood by marine toxins has been a consistent public health
problem. Gymnodimine (GYM) is a member of a family of spirocyclic imine containing
marine natural products which was shown to be highly toxic (LD50 96 mg/kg,
intraperitoneal injection); thus ensuring public safety requires stringent monitoring of
gymnodimine. Current detection methods for GYM and spirolides include the mouse
bioassay and LC-MS-based detection techniques which, however, have significant
limitations. Therefore, more efficient and convenient detection methods are required.
Building on our recently completed total synthesis of (-)-gymnodimine, the synthesis of
two haptens were targeted for eventual production of monoclonal antibodies (mAb) to be
used in an eventual Enzyme-Linked Immunosorbent Assay (ELISA) for gymnodimine.
As an extension of the intramolecular nucleophilic catalyzed aldol lactonization
(NCAL) process from aldehyde acid to keto acid substrates, carbocyclic and nitrogen
heterocyclic B-lactones were synthesized. Demonstration of the utility of the NCAL
process for keto acids was applied to the synthesis of dihydroplakevulin A and the core of
tussilagine. In addition, although initial attempts to develop guanidine catalysts for the
asymmetric NCAL process were unsuccessful, homobenzotetramisole (HBTM) was
found to be a suitable asymmetric catalyst for keto acid substrates.
Finally, synthetic studies toward the proposed structure of thiolyngbyan are
described. Thiolyngbyan was isolated from a blue-green algae and it exhibited antifungal
activity. | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | en_US | |
dc.subject | Gymnodimine | en |
dc.subject | hapten | en |
dc.subject | beta-lactone | en |
dc.subject | heterocycles | en |
dc.subject | thiolyngbyan | en |
dc.title | Synthesis of Haptens for the Marine Toxin, Gymnodimine; Synthesis of Beta-lactone Fused Carbocycles and Nitrogen Heterocycles; Efforts Toward the Synthesis of the Proposed Structure of Thiolyngbyan | en |
dc.type | Thesis | en |
thesis.degree.department | Chemistry | en |
thesis.degree.discipline | Chemistry | en |
thesis.degree.grantor | Texas A&M University | en |
thesis.degree.name | Doctor of Philosophy | en |
thesis.degree.level | Doctoral | en |
dc.contributor.committeeMember | Watanabe, Coran M. | |
dc.contributor.committeeMember | Versaw, Wayne K. | |
dc.contributor.committeeMember | Singleton, Daniel A. | |
dc.type.genre | thesis | en |
dc.type.material | text | en |