ǂa ǂtool for enhancing the local hydrophobicity of peptides
Jure Gregorc (Avtor), Nathalie Lensen (Avtor), Grégory Chaume (Avtor), Jernej Iskra (Avtor), Thierry Brigaud (Avtor)

Povzetek

The incorporation of fluorinated groups into peptides significantly affects their biophysical properties. We report herein the synthesis of Fmoc-protected trifluoromethylthiolated tyrosine (CF$_3$S-Tyr) and tryptophan (CF$_3$S-Trp) analogues on a gram scale (77–93% yield) and demonstrate their use as highly hydrophobic fluorinated building blocks for peptide chemistry. The developed methodology was successfully applied to the late-stage regioselective trifluoromethylthiolation of Trp residues in short peptides (66–80% yield) and the synthesis of various CF$_3$S-analogues of biologically active monoamines. To prove the concept, Fmoc-(CF$_3$S)Tyr and -Trp were incorporated into the endomorphin-1 chain (EM-1) and into model tripeptides by solid-phase peptide synthesis. A remarkable enhancement of the local hydrophobicity of the trifluoromethylthiolated peptides was quantified by the chromatographic hydrophobicity index determination method, demonstrating the high potential of CF$_3$S-containing amino acids for the rational design of bioactive peptides.

Ključne besede

aromatske spojine;hidrofobnost;monomeri;peptidi;proteini;reakcijski produkti;aromatic compounds;hydrophobicity;monomers;peptides;proteins;reaction products;

Podatki

Jezik: Angleški jezik
Leto izida:
Tipologija: 1.01 - Izvirni znanstveni članek
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
UDK: 547.1-32-304.2:66.095.253
COBISS: 171743491 Povezava se bo odprla v novem oknu
ISSN: 0022-3263
Št. ogledov: 85
Št. prenosov: 8
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Slovenski jezik
Sekundarne ključne besede: aromatske spojine;hidrofobnost;monomeri;peptidi;proteini;reakcijski produkti;
Vrsta dela (COBISS): Članek v reviji
Strani: str. 13169-13177
Letnik: ǂVol. ǂ88
Zvezek: ǂiss. ǂ18
Čas izdaje: 15 Sep. 2023
DOI: 10.1021/acs.joc.3c01373
ID: 20959969