Copper-mediated peptide arylation selective for the N-terminus
- Resource Type
- Authors
- Zachary T. Ball; Olivia Zhang; Mary K. Miller; Alex Berlaga; Kengo Hanaya; Haopei Wang
- Source
- Chemical Science
- Subject
- chemistry.chemical_classification
Aqueous solution
Lysine
Peptide
General Chemistry
Combinatorial chemistry
N-terminus
Chemistry
chemistry.chemical_compound
chemistry
Amine gas treating
Reactivity (chemistry)
Selectivity
Boronic acid
- Language
- ISSN
- 2041-6539
2041-6520
Polypeptides present remarkable selectivity challenges for chemical methods. Amino groups are ubiquitous in polypeptide structure, yet few paradigms exist for reactivity and selectivity in arylation of amine groups. This communication describes the utilization of boronic acid reagents bearing certain o-electron withdrawing groups for copper-mediated amine arylation of the N-terminus under mild conditions and primarily aqueous solvent. The method adds to the toolkit of boronic acid reagents for polypeptide modification under mild conditions in water that shows complete selectivity for the N-terminus in the presence of lysine side chains.
The discovery of unique Chan-Lam coupling reactivity of arylboronic acids containing an ortho-sulfonamide group allows site-specific tailoring of peptide structure.