Matic Proj (Avtor), Nika Strašek (Avtor), Stane Pajk (Avtor), Damijan Knez (Avtor), Izidor Sosič (Avtor)

Povzetek

The binucleophilic properties of 1,2-aminothiol and its rare occurrence in nature make it a useful reporter for tracking molecules in living systems. The 1,2-aminothiol moiety is present in cysteine, which is a substrate for a biocompatible click reaction with heteroaromatic nitriles. Despite the wide range of applications for this reaction, the scope of nitrile substrates has been explored only to a limited extent. In this study, we expand the chemical space of heteroaromatic nitriles for bioconjugation under physiologically relevant conditions. We systematically assembled a library of 116 2-cyanobenzimidazoles, 1-methyl-2-cyanobenzimidazoles, 2-cyanobenzothiazoles, and 2-cyanobenzoxazoles containing electron-donating and electron-withdrawing substituents at all positions of the benzene ring. The compounds were evaluated for their stability, reactivity, and selectivity toward the N-terminal cysteine of model oligopeptides. In comparison to the benchmark 6-hydroxy-2-cyanobenzothiazole or 6-amino-2-cyanobenzothiazole, we provide highly selective and moderately reactive nitriles as well as highly reactive yet less selective analogs with a variety of enabling attachment chemistries to aid future applications in bioconjugation, chemical biology, and nanomaterial science.

Ključne besede

označevanje;monomeri;dušikove spojine;peptidi;proteini;reaktivnost;labeling;monomers;nitrogen compounds;peptides;reactivity;proteins;

Podatki

Jezik: Angleški jezik
Leto izida:
Tipologija: 1.01 - Izvirni znanstveni članek
Organizacija: UL FFA - Fakulteta za farmacijo
UDK: 615.4:54
COBISS: 156888323 Povezava se bo odprla v novem oknu
ISSN: 1043-1802
Št. ogledov: 228
Št. prenosov: 32
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: Peptidi;Farmacevtska kemija;Proteini;
Vrsta dela (COBISS): Članek v reviji
Strani: str. 1271-1281
Letnik: ǂVol. ǂ34
Zvezek: ǂno. ǂ7
Čas izdaje: 2023
DOI: 10.1021/acs.bioconjchem.3c00163
ID: 19747909