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Tunable heteroaromatic nitriles for selective bioorthogonal click reaction with cysteineProj, Matic ...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.Source: Bioconjugate chemistry. - ISSN 1043-1802 (Vol. 34, no. 7, 2023, str. 1271-1281)Type of material - article, component part ; adult, seriousPublish date - 2023Language - englishCOBISS.SI-ID - 156888323
Author
Proj, Matic |
Strašek Benedik, Nika |
Pajk, Stane, 1983- |
Knez, Damijan, farmacevt |
Sosič, Izidor
Topics
Peptidi |
Farmacevtska kemija |
Proteini |
označevanje |
monomeri |
dušikove spojine |
peptidi |
proteini |
reaktivnost |
labeling |
monomers |
nitrogen compounds |
peptides |
reactivity |
proteins
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Author | Proj, Matic ... |
Title | Tunable heteroaromatic nitriles for selective bioorthogonal click reaction with cysteine |
Publication date | 2023-06-24 |
COBISS.SI-ID | 156888323 |
Publication version in repository | Publisher's version |
Publication licence | Creative Commons Attribution 4.0 International |
Embargo | Immediate publication for public |
Project(s) from which the publication was funded
Title | Acronym | Project ID | Funder |
---|---|---|---|
Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin | P1-0208-2022 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
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Database name | Field | Year |
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Proj, Matic | 52376 |
Strašek Benedik, Nika | 52378 |
Pajk, Stane, 1983- | 28861 |
Knez, Damijan, farmacevt | 36438 |
Sosič, Izidor | 30816 |
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