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: |
2023 |
Tipologija: |
1.01 - Izvirni znanstveni članek |
Organizacija: |
UL FFA - Fakulteta za farmacijo |
UDK: |
615.4:54 |
COBISS: |
156888323
|
ISSN: |
1043-1802 |
Št. ogledov: |
228 |
Št. prenosov: |
32 |
Ocena: |
0 (0 glasov) |
Metapodatki: |
|
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 |