Article ; Online: Selective Late-Stage Functionalization of Tryptophan-Containing Peptides To Facilitate Bioorthogonal Tetrazine Ligation.
Organic letters
2024 Volume 26, Issue 12, Page(s) 2489–2494
Abstract: Site-selective modification of complex peptides and the functionalization of their C-H bonds hold great promise for expanding their use in therapeutics and biomedical research. Herein, we leverage the power of late-stage chemoenzymatic catalysis using an ...
Abstract | Site-selective modification of complex peptides and the functionalization of their C-H bonds hold great promise for expanding their use in therapeutics and biomedical research. Herein, we leverage the power of late-stage chemoenzymatic catalysis using an indole prenyltransferase (IPT) enzyme and alkyl diphosphates to specifically modify the indole ring of tryptophan in clinically relevant peptides. Furthermore, the installed handle enables bioorthogonal click chemistry through an inverse electron-demand Diels-Alder (IEDDA) reaction with a biotin-conjugated tetrazine probe. |
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MeSH term(s) | Tryptophan ; Peptides ; Cycloaddition Reaction ; Heterocyclic Compounds ; Indoles |
Chemical Substances | Tryptophan (8DUH1N11BX) ; Peptides ; Heterocyclic Compounds ; Indoles |
Language | English |
Publishing date | 2024-03-18 |
Publishing country | United States |
Document type | Journal Article |
ISSN | 1523-7052 |
ISSN (online) | 1523-7052 |
DOI | 10.1021/acs.orglett.4c00709 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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