Late-stage functionalisation of peptides on the solid phase by an iodination-substitution approach
The functionalisation of peptides at a late synthesis stage holds great potential, for example, for the synthesis of peptide pharmaceuticals, fluorescent biosensors or peptidomimetics. Here we describe an on-resin iodination-substitution reaction sequence on homoserine that is also suitable for pept...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
September 6, 2022
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| In: |
Chemistry - a European journal
Year: 2022, Volume: 28, Issue: 50, Pages: 1-7 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202201339 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202201339 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202201339 
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| Author Notes: | Marius Werner, Julius Pampel, Truc Lam Pham, and Franziska Thomas |
MARC
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| 520 | |a The functionalisation of peptides at a late synthesis stage holds great potential, for example, for the synthesis of peptide pharmaceuticals, fluorescent biosensors or peptidomimetics. Here we describe an on-resin iodination-substitution reaction sequence on homoserine that is also suitable for peptide modification in a combinatorial format. The reaction sequence is accessible to a wide range of sulfur nucleophiles with various functional groups including boronic acids, hydroxy groups or aromatic amines. In this way, methionine-like thioethers or thioesters and thiosulfonates are accessible. Next to sulfur nucleophiles, selenols, pyridines and carboxylic acids were successfully used as nucleophiles, whereas phenols did not react. The late-stage iodination-substitution approach is not only applicable to short peptides but also to the more complex 34-amino-acid WW domains. We applied this strategy to introduce 7-mercapto-4-methylcoumarin into a switchable ZnII responsive WW domain to design an iFRET-based ZnII sensor. | ||
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