Delgado, Jose A. C. and Tian, Ya-Ming and Marcon, Michela and Koenig, Burkhard and Paixao, Marcio W. (2023) Side-Selective Solid-Phase Metallaphotoredox N(in)-Arylation of Peptides. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 145 (48). pp. 26452-26462. ISSN 0002-7863, 1520-5126
Full text not available from this repository. (Request a copy)Abstract
Postsynthetic diversification of peptides through selective modification of endogenous amino acid side chains has enabled significant advances in peptide drug discovery while expanding the biological and medical chemistry space. However, current tools have been focused on the modification of reactive polar and ionizable side chains, whereas the decoration of aromatic systems (e.g., the N-(in) of the tryptophan) has been a long-standing challenge. Here, we introduce metallaphotocatalysis in solid-phase peptide synthesis for the on-resin orthogonal N-arylation of relevant tryptophan-containing peptides. The protocol allows the chemoselective introduction of a new C(sp(2))-N bond at the N-(in) of tryptophan in biologically active protected peptide sequences in the presence of native redox-sensitive side chains. The fusion of metallaphotocatalysis with solid-phase peptide synthesis opens new perspectives in diversifying native amino acid side chains.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-H FUNCTIONALIZATION; ARYL; PHOTOREDOX; CATALYSIS; ELECTROPHILES; ACIDS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Mar 2024 11:53 |
| Last Modified: | 12 Mar 2024 11:53 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59781 |
Actions (login required)
 |
View Item |
