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DOI: 10.1055/a-2091-8062
Exploring Chemical Modifications of Aromatic Amino Acid Residues in Peptides
M.S.M. gratefully acknowledges the Council of Scientific and Industrial Research, India (Grant no. 02(0433)/21/EMR-II) for funding. B.P sincerely thanks the Department of Science and Technology, Science and Engineering Research Board (DST-SERB) of India (Grant no. SUR/2022/001257) for financial support. B.P. also acknowledges the University Grants Commission, Faculty Recharge Progamme (UGC-FRP) and Bangalore University (U.O DEV:D2a:BU-RP:2020-21) for funding. S.B. and G.K. thank the CSIR, India for fellowships. M.P. thanks the DST, Government of India, for financial support (Grant no. SR/WOS-A/CS-8/2017) under the Women Scientists Scheme.
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Abstract
The chemical diversification of biomolecules set forth a significant area of research that constitutes an important intersection between chemistry and biology. Amino acids and peptides are the fundamental building blocks of proteins and play essential roles in all living organisms. While significant efforts have been geared toward the chemical modification of amino acid residues, particularly the functionalization of reactive functional groups such as lysine NH2 and cysteine SH, the exploration of the aromatic amino acid residues of tryptophan, tyrosine, phenylalanine, and histidine has been relatively limited. Therefore, this review highlights strategies for the side-chain functionalization of these four aromatic amino acids in peptides, with a focus on elucidating the underlying mechanisms. We have also illustrated the use of these modifications in the chemical and biological realm.
1 Introduction
2 Tryptophan Modifications
3 Tyrosine Modifications
4 Phenylalanine Modifications
5 Histidine Modifications
6 Perspectives and Future Outlook
Key words
aromatic amino acids - bioconjugation chemistry - C–H functionalization - macrocyclization - photocatalysis - side-chain modifications - transition-metal catalysisPublikationsverlauf
Eingereicht: 09. April 2023
Angenommen nach Revision: 11. Mai 2023
Accepted Manuscript online:
11. Mai 2023
Artikel online veröffentlicht:
19. Juni 2023
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