Type
Text
Type
Thesis
Advisor
Parker, Kathlyn | Laughlin, Scott. | Carrico, Isaac.
Date
2017-08-01
Keywords
Chemistry | click chemistry | cyclopropene | dopamine analog | spirocyclopropene
Department
Department of Chemistry.
Language
en_US
Source
This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree
Identifier
http://hdl.handle.net/11401/78345
Publisher
The Graduate School, Stony Brook University: Stony Brook, NY.
Format
application/pdf
Abstract
Click and bioorthogonal chemistry has been employed in the analysis of many biological systems, but has yet to be extended to the analysis of neural connectivity1. One popular bioorthogonal chemical reporter is the functionalized cyclopropene, which reacts with tetrazines through an inverse electron-demand Diels-Alder reaction2. Here, I describe a strategy for leveraging the cyclopropene-tetrazine ligation for analysis of neural systems and a novel photo-activatable cyclopropene for controlling reactivity in space and time. My first project employs a dopamine analog consisting of a neurotransmitter attached to a cyclopropene tag to study the dopaminergic neural circuit. I designed and synthesized three different cyclopropene-bearing dopamine analogs. These molecules will enable visualization of dopaminergic vesicles and connected neurons, when they are released into the synaptic space. My second project involves developing a new, activatable, bio-orthogonal reagent. I have synthesized a spirocyclopropene that is non-reactive when protected with a light cleavable group, but reactive towards tetrazine reagents one the group is removed by light. Ultimately, this strategy will enable controlled bioorthogonal reactivity that will permit the development of imaging tools for visualizing neural connectivity. | 84 pages
Recommended Citation
Li, Sining, "Novel cyclopropenes for studying biological systems" (2017). Stony Brook Theses and Dissertations Collection, 2006-2020 (closed to submissions). 3839.
https://commons.library.stonybrook.edu/stony-brook-theses-and-dissertations-collection/3839