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| Auteurs principaux: | , , , |
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| Format: | Artículo científico |
| Langue: | en |
| Publié: |
Journal of the American Chemical Society
2025
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| Sujets: | |
| Accès en ligne: | https://pubmed.ncbi.nlm.nih.gov/40958471/ |
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Table des matières:
- Late-Stage Tryptophan Modification of Native Peptides through Photochemical Indole-to-Quinazoline Editing. Li, Heng-Hui Xiao, Yisa Liu, Han Li, Xuechen Tryptophan Indoles Quinazolines Peptides Photochemical Processes Oxidation-Reduction Molecular Structure Site-specific late-stage modification of native peptides is an appealing strategy for generating analogues of bioactive peptides in an effort- and cost-effective manner. The concept of skeletal editing emerging recently is attractive for developing a new generation of late-stage peptide modification methods. In this work, we developed a facile tryptophan-specific late-stage peptide modification based on photocatalytic indole-to-quinazoline editing. The method showed a broad scope regarding both linear and cyclic peptide substrates and was applied to the modification of commercially available peptide drugs. A mechanism based on singlet oxygen oxidation of tryptophan and the interruption of oxidative indole cleavage by ammonia addition was proposed.