Reductant-Induced Free Radical Fluoroalkylation of Nitrogen Heterocycles and Innate Aromatic Amino Acid Residues in Peptides and Proteins.
Chemistry
; 25(69): 15779-15785, 2019 Dec 10.
Article
en En
| MEDLINE
| ID: mdl-31523878
ABSTRACT
A series of fluoroalkylated cyclic λ3 -iodanes and their hydrochloride salts was prepared and used in a combination with sodium ascorbate in buffer or aqueous methanol mixtures for radical fluoroalkylation of a range of substituted indoles, pyrroles, tryptophan or its derivatives, and Trp residues in peptides. As demonstrated on several peptides, the aromatic amino acid residues of Trp, Tyr, Phe, and His are targeted with high selectivity to Trp. The functionalization method is biocompatible, mild, rapid, and transition-metal-free. The proteins myoglobin, ubiquitin, and human carbonic anhydraseâ
I were also successfully functionalized.
Palabras clave
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Péptidos
/
Pirroles
/
Proteínas
/
Aminoácidos Aromáticos
/
Indoles
Límite:
Humans
Idioma:
En
Año:
2019
Tipo del documento:
Article