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Design and development of novel organocatalytic artificial enzymes

Santi, Nicolo ORCID: 2020. Design and development of novel organocatalytic artificial enzymes. PhD Thesis, Cardiff University.
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The creation of organocatalysts which function efficiently in aqueous or biocompatible environments can be useful for different applications, including soft robotics, self-healing materials, controlled drug delivery or on-demand drug synthesis in tumour cells. Thus, enabling organocatalysis under biologically benign conditions is still an essential challenge in chemical biology. This work aims to create a family of streptavidin-based artificial enzymes able to mediate organocatalysis in a biocompatible environment. Inspired by previous work in our group, the streptavidin-biotin technology was used to design organocatalytic artificial enzymes for iminium and enamine catalysis. In particular, two different proteins, tetrameric streptavidin (Sav) and its monomeric variant (M-Sav) were tested as hosts using the biotinylated organocatalyst 73 and 74 as ligands. In the first part of this work, two novel artificial enzymes, M-Sav:73 and M-Sav:74, were created and tested for iminium catalysis. In the second part, Sav:73 was employed for iminium catalysed transfer hydrogenations, whereas in the last chapter enamine catalysis was performed using Sav:73 complex. Furthermore, optimisation of the protein scaffolds was carried out to design artificial enzymes with improved activity and selectivity. Moreover, an insight into the mechanism of action of these artificial complexes was provided.

Item Type: Thesis (PhD)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 29 January 2021
Last Modified: 09 Nov 2022 10:03

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