Journal
ORGANIC LETTERS
Volume 22, Issue 5, Pages 1754-1759Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00033
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Funding
- MINECO [RTI2018-093721-B-I00]
- Basque Government [IT1033-16]
- SGIker of UPV/EHU
- European funding (ERDF and ESF)
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Site-selective functionalization of C-H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp(2))-H trifluoromethylation of tryptophan (Trp)-containing peptides. This fluorination technique is characterized by its chirality preservation, tolerance of functional groups, and scalability and exhibits chemoselectivity for Trp residues over other amino acid and heterocyclic units. As a result, it represents a sustainable tool toward the late-stage peptide modification and protein engineering.
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