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  • Tunable heteroaromatic nitriles for selective bioorthogonal click reaction with cysteine
    Proj, 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, serious
    Publish date - 2023
    Language - english
    COBISS.SI-ID - 156888323

    Link(s):

    https://pubs.acs.org/doi/10.1021/acs.bioconjchem.3c00163
    Repository of the University of Ljubljana – RUL
    DOI

source: Bioconjugate chemistry. - ISSN 1043-1802 (Vol. 34, no. 7, 2023, str. 1271-1281)
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