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Rational design and synthesis of novel amino-luciferin analogues

Pumpianskii, Mikhail; (2022) Rational design and synthesis of novel amino-luciferin analogues. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

Firefly luciferin, also known as D-luciferin, is a naturally occurring bioluminescent compound, found in various insects. This small molecule and its synthetic analogues have been used for bioluminescent imaging (BLI). This thesis presents the synthesis of novel D-luciferin analogues that incorporate an amine functional group, to explore the development of red-shifted and brighter analogues. The opening chapter of this thesis discusses the history of bioluminescence and its studies. There is then a greater focus on the history of D-luciferin and luciferase enzyme, as well as the effect various changes to either of the two components has on the bioluminescence. A review of synthetic analogues of D-luciferin, previously reported in the literature, including their bioluminescent properties is presented. The introduction ends with a discussion of the current challenges in the field of bioluminescent reporters and the aim of this project to explore novel amine-based analogues to explore improved emission wavelength and brightness of existing analogues. The second chapter discusses the synthesis of novel amine infra-luciferin analogues. This chapter presents a convergent synthesis of amine infra-luciferin analogues. The third chapter details the synthesis of a C-4 substituted amine D-luciferin analogue. A variety of attempted methods to construct the benzothiazole moiety are discussed. The fourth chapter summarises the results and suggests future work for both the amine infra-luciferins and the C-4 substituted amine luciferin, as well as outlines of potential future work. The final chapter presents experimental procedures and analytical data. The thesis is fully referenced to the primary literature.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Rational design and synthesis of novel amino-luciferin analogues
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Copyright © The Author 2022. Original content in this thesis is licensed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) Licence (https://creativecommons.org/licenses/by-nc/4.0/). Any third-party copyright material present remains the property of its respective owner(s) and is licensed under its existing terms. Access may initially be restricted at the author’s request.
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10150182
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