Type
Text
Type
Thesis
Advisor
Lauher, Joseph | Drueckhammer, Dale | Rudick, Jonathan.
Date
2016-12-01
Keywords
Chemistry -- Organic chemistry | arsenic, foldamer
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/11401/77016
Publisher
The Graduate School, Stony Brook University: Stony Brook, NY.
Format
application/pdf
Abstract
Arsenic is a known harmful chemical, causing cancer and other adverse health effects if consumed in even modest amounts. Arsenic is found in drinking water at levels higher than deemed safe in many parts of the world. Current detection methods for arsenic in water have many limitations. A low-cost, safe, and efficient alternative would make arsenic detection simpler and human lives safer. As arsenic is known to have a high affinity to sulfur, the Drueckhammer group has designed a compound with two protruding thiol groups that may provide the basis for fluorescence-based detection. In this study, preliminary steps in the proposed synthesis of the designed arsenic receptor have been performed. An initial intermediate has been synthesized via reaction that forms a Grignard intermediate and generates benzyne in situ, followed by a Diels Alder reaction. An additional intermediate has also been synthesized via a Grubbs II-catalyzed reaction of the aforementioned Diels Alder product to yield a less strained alkene that may be more reactive in the subsequent steps. Various methods of double-bond ring cleavage and alkene oxidation have been explored. Ozonolysis seemed most promising in its efficiency and yield but unfortunately no success was seen with either starting material. Another approach of oxidative cleavage was explored with much success and has allowed the proposed synthetic pathway to progress further. In conjunction with this project, additional work was performed on a separate project in hopes of developing a pi-stacking polyamide oligomer. A synthetic pathway toward nucleic acid mimics is being pursued by another student in the lab, and it is possible for this pathway to branch off into another synthesis to possibly develop a foldamer molecule. Foldamer chemistry strives to understand how proteins fold and maintain certain structures, and how that can be reproduced synthetically. Being able to synthetically replicate interactions such as protein folding is a thriving field as its success can be used for the cure and treatment of diseases, most notably, cancer. | 67 pages
Recommended Citation
Castro, Dana Michele, "Synthetic Approaches to a Bis-Thiol based Arsenic Receptor and a Potential Pi-Stacking based Polyamide Foldamer" (2016). Stony Brook Theses and Dissertations Collection, 2006-2020 (closed to submissions). 2877.
https://commons.library.stonybrook.edu/stony-brook-theses-and-dissertations-collection/2877