Bachelor with Honours Dissertations - open access

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https://hdl.handle.net/10292/14987
The "Bachelor with Honours Dissertations - open access" collection contains digital copies of AUT University B(Hons) dissertations approved for open access. B(Hons) dissertations are required to be open access from April 2022. Past students may contact the Tuwhera team (tuwhera.opentheses@aut.ac.nz) if they wish to make their B(Hons) open access.

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Browsing Bachelor with Honours Dissertations - open access by Author "Chen, Jack"

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    Phosphate Sensors Formed by the Self-Assembly of Fluorescent Probes
    (Auckland University of Technology, 2022) Matich, Olivia; Chen, Jack
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    Synthesis of Enzyme Inspired Immobilized Catalysts
    (Auckland University of Technology, 2023) Malingin, Marc; Chen, Jack
    The primary objective of this study is to develop an immobilized catalyst for transphosphorylation, drawing inspiration from enzymatic processes. To accomplish this goal, a set of key objectives were set. Firstly, the synthesis of TACN (A) and guanidinium (B) ligands is paramount. Then, the next objective is to immobilize these ligands onto a solid resin, establishing a bioactive site through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click reaction." Lastly, the study aims to evaluate the catalytic activity of these supported catalysts using the model substrate HPNPP. This assessment seeks to identify optimal conditions for catalytic activation and to elucidate potential cooperativity in the catalytic process. The focus of this project lies in investigating the catalytic properties of the selected ligands when immobilized on solid resin as an alternative to gold nanoparticles. The investigation includes the characterization of molecules, monitoring reactions through NMR and IR spectroscopy, and evaluating catalytic activity using UV-vis spectroscopy. TACN (A) was initially synthesized using a protective group, Boc, and this was employed to selectively perform a substitution reaction at the desired site. Subsequently, "click chemistry" was utilized to attach it to the resin. Finally, the protective group was cleaved under acidic conditions. The synthesis of Guanidinium (B) was approached through three distinct routes. The first route involved a standard substitution reaction, followed by a Staudinger reduction reaction, ending in guanylation. In the second route, with the aim of enhancing efficiency and effectiveness, a different starting material was used and tosylation was performed before following the aforementioned steps. The third route employed a completely different route, employing Gabriel synthesis to obtain the amine, which was eventually subjected to guanylation. Similar to the TACN synthesis, the "click reaction" was employed to immobilize the ligands, and deprotection was achieved through acidic conditions. We successfully showcased the immobilization of different functional groups onto the Merrifield resin's surface, resulting in the creation of a highly efficient transphosphodiesterase. This achievement holds promise for applications in synthesizing artificial enzymes characterized by great stability compared to their biological counterparts, along with the convenience of recovery and reusability. Our future research endeavors will focus on further enhancing this technology by exploring combinations of the two existing ligands and potentially introducing additional ligands in varying proportions, with the aim of developing artificial enzymes boasting even greater catalytic activities.
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    The Synthesis of Phenol Glycosides as Markers for Smoke Taint in Wine
    (Auckland University of Technology, 2022) D'souza, Shaun; Chen, Jack
    Wildfires can cause a number of different issues for the winemaker such as damages to crops and property, with the biggest issue being economic losses due to smoke-tainted wine. This project looked into finding a lasting solution to the problem of smoke-tainted wine. The main aim of this project was to synthesise the novel phenolic glycoside, para-cresol gentiobioside, which is one on many compounds that are responsible for smoke taint in wine. The compound, when synthesised will then be used by the industrial collaborators involved in this project to develop molecularly imprinted polymers to selectively remove the same or other closely-related compounds. All reactions in the proposed synthetic scheme for para-cresol gentiobioside were performed and were also optimised where necessary to obtain a better yield at that step. 0.0750 grams of the novel compound, para-cresol gentiobioside was successfully synthesised in this project. In the final stages of the project an alternative synthetic route which was more efficient and which could potentially provide faster access to other phenolic glycosides responsible for smoke taint was explored.
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