Reductant-Induced Free Radical Fluoroalkylation of Nitrogen Heterocycles and Innate Aromatic Amino Acid Residues in Peptides and Proteins
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
61388963
Ústav Organické Chemie a Biochemie, Akademie Věd České Republiky
61388971
Akademie Věd České Republiky
17-00598S
Grantová Agentura České Republiky
19-16084S
Grantová Agentura České Republiky
LM2015043 CIISB
Ministerstvo Školství, Mládeže a Tělovýchovy
CZ.1.05/1.1.00/02.0109 BIOCEV
European Regional Development Fund
PubMed
31523878
DOI
10.1002/chem.201902944
Knihovny.cz E-zdroje
- Klíčová slova
- bioconjugation, fluorine, iodine, radicals, tryptophan,
- MeSH
- alkylace MeSH
- aminokyseliny aromatické chemická syntéza chemie MeSH
- halogenace MeSH
- indoly chemická syntéza chemie MeSH
- lidé MeSH
- molekulární modely MeSH
- peptidy chemická syntéza chemie MeSH
- proteiny chemická syntéza chemie MeSH
- pyrroly chemická syntéza chemie MeSH
- volné radikály chemická syntéza chemie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- aminokyseliny aromatické MeSH
- indoly MeSH
- peptidy MeSH
- proteiny MeSH
- pyrroly MeSH
- volné radikály MeSH
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 anhydrase I were also successfully functionalized.
CF Plus Chemicals s r o Karásek 1767 1 62100 Brno Řečkovice Czech Republic
Institute of Microbiology Czech Academy of Sciences Vídeňská 1083 14200 Prague 4 Czech Republic
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