Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification
A chemoselective peptide functionalisation strategy via photocatalytic tryptophan (Trp) modification has been developed. The versatility of the reaction is demonstrated by tethering a variety of difluoroalkyl groups to Trp using an organic photocatalyst and short irradiation times with visible light...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2024
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| Online Access: | https://eprints.nottingham.ac.uk/78245/ |
| _version_ | 1848801062052429824 |
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| author | Lee, Joanna |
| author_facet | Lee, Joanna |
| author_sort | Lee, Joanna |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | A chemoselective peptide functionalisation strategy via photocatalytic tryptophan (Trp) modification has been developed. The versatility of the reaction is demonstrated by tethering a variety of difluoroalkyl groups to Trp using an organic photocatalyst and short irradiation times with visible light. Due to the mild and biocompatible reaction conditions, a range of complex peptides have been successfully functionalised to give a diverse library of small molecule-peptide conjugates. Results have confirmed site-selectivity for Trp in the presence of other amino acids, illustrating that this transformation can expand the field of chemoselective photo-bioconjugation. Applications of the methodology have been explored including protein modification and peptide stapling. For the latter, incorporation of the bromodifluorocarbonyl moiety into the peptide sequence during solid phase peptide synthesis (SPPS), enabled the synthesis of macrocyclic peptides. |
| first_indexed | 2025-11-14T21:01:28Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-78245 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:01:28Z |
| publishDate | 2024 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-782452024-07-24T04:43:55Z https://eprints.nottingham.ac.uk/78245/ Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification Lee, Joanna A chemoselective peptide functionalisation strategy via photocatalytic tryptophan (Trp) modification has been developed. The versatility of the reaction is demonstrated by tethering a variety of difluoroalkyl groups to Trp using an organic photocatalyst and short irradiation times with visible light. Due to the mild and biocompatible reaction conditions, a range of complex peptides have been successfully functionalised to give a diverse library of small molecule-peptide conjugates. Results have confirmed site-selectivity for Trp in the presence of other amino acids, illustrating that this transformation can expand the field of chemoselective photo-bioconjugation. Applications of the methodology have been explored including protein modification and peptide stapling. For the latter, incorporation of the bromodifluorocarbonyl moiety into the peptide sequence during solid phase peptide synthesis (SPPS), enabled the synthesis of macrocyclic peptides. 2024-07-24 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/78245/1/Lee%20Joanna%2014249733%20Corrections.pdf Lee, Joanna (2024) Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification. PhD thesis, University of Nottingham. peptides peptide functionalisation biomolecules |
| spellingShingle | peptides peptide functionalisation biomolecules Lee, Joanna Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification |
| title | Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification |
| title_full | Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification |
| title_fullStr | Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification |
| title_full_unstemmed | Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification |
| title_short | Photocatalytic Tryptophan Alkylation for Chemoselective Peptide Modification |
| title_sort | photocatalytic tryptophan alkylation for chemoselective peptide modification |
| topic | peptides peptide functionalisation biomolecules |
| url | https://eprints.nottingham.ac.uk/78245/ |