Progress towards a total synthesis of the bis-guanidinium neurotoxin zetekitoxin AB
Abstract/Contents
- Abstract
- Zetekitoxin AB (ZTX) is a potent neurotoxin isolated from the endangered Panamanian golden frog, Atelopus zeteki. ZTX belongs to a family of bis-guanidinium toxins, which includes (+)-saxitoxin (STX) and the gonyautoxins (GTXs). ZTX, however, is ~200 times more potent than STX as an inhibitor of voltage-gated sodium ion channels (NaVs). Two structural features are unique to ZTX: a bridging macrolactam and an unusual guanidinium N,O-acetal. Given that the total isolate supply of ZTX is 300 μg, de novo synthesis of ZTX is the only way to enable structure-activity studies and to confirm the assigned structure. To this end, a route to the tricyclic core of ZTX has been developed to enable access to the natural product. This route also provides access to the related bis-guanidinium toxin GTX.
Description
| Type of resource | text |
|---|---|
| Form | electronic resource; remote; computer; online resource |
| Extent | 1 online resource. |
| Place | California |
| Place | [Stanford, California] |
| Publisher | [Stanford University] |
| Copyright date | 2023; ©2023 |
| Publication date | 2023; 2023 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Clay, Alyssa Paige |
|---|---|
| Degree supervisor | Du Bois, Justin |
| Thesis advisor | Du Bois, Justin |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Wender, Paul A |
| Degree committee member | Burns, Noah |
| Degree committee member | Wender, Paul A |
| Associated with | Stanford University, School of Humanities and Sciences |
| Associated with | Stanford University, Department of Chemistry |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Alyssa Clay. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2023. |
| Location | https://purl.stanford.edu/rf279hh5336 |
Access conditions
- Copyright
- © 2023 by Alyssa Paige Clay
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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