Synthesis of the ladderane lipids
Abstract/Contents
- Abstract
- The ladderane phospholipids are perhaps the most structurally unique membrane lipids in the natural world. They are produced exclusively by anaerobic ammonium oxidizing (anammox) bacteria and are theorized to form dense, impermeable bilayers, but the role these lipids play in anammox membranes has not been determined. A synthetic campaign to prepare both ladderane lipid tails and a selection of natural and unnatural ladderane phospholipids comprises the bulk of this dissertation. Expedient, enantioselective routes to both [5]-ladderane and [3]-ladderane lipids have been developed. As part of this campaign, the absolute stereochemical configuration of natural [3]-ladderane lipid tails was established by comparison to natural material. The dissertation also contains two collaborative projects. First, the biophysical properties of our synthetic ladderane phospholipids were thoroughly explored. We established a structure-function relationship for the ladderane lipid tails and provided evidence that the ladderane phospholipids serve to slow proton diffusion across anammox membranes. Second, we developed the synthesis of a poly(ladderene) material comprised of monomers based on the [5]-ladderane scaffold. The polymer undergoes a dramatic structural rearrangement in response to mechanical force, converting from an insulating to a conducting organic material.
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 | 2018; ©2018 |
| Publication date | 2018; 2018 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Mercer, Jaron A. M |
|---|---|
| Degree supervisor | Burns, Noah |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Du Bois, Justin |
| Thesis advisor | Kanan, Matthew William, 1978- |
| Degree committee member | Du Bois, Justin |
| Degree committee member | Kanan, Matthew William, 1978- |
| Associated with | Stanford University, Department of Chemistry. |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Jaron A. M. Mercer. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2018. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2018 by Jaron August McClure Mercer
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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