ArticleBioconjugate chemistry2023
Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine.
Article in Bioconjugate chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 15 citations in OpenAlex.
- Article
- Toward Precision Bioconjugation: Chemical Strategies for Site-Selective Cysteine Conjugation.Precision chemistry · 2026Review
- Article
- Tunable Linkers for Dynamic Thiol-Based Bioconjugation Strategies.Biomacromolecules · 2026Review
- Modular Synthesis of Pyritide-Inspired Macrocycles Featuring Bipyridine Motifs.Angewandte Chemie (International ed. in English) · 2025Article
- Ammoxidation of Unprotected Glycosides: A One-Pot Conversion of Alcohols to Nitriles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Glutathione in the Biosynthesis of Glutazoline Teredinibactins.Organic letters · 2025Article
- Light-Controlled Intracellular Synthesis of Poly(luciferin) Polymers Induces Cell Paraptosis.Journal of the American Chemical Society · 2025Article
- 2-cyanopyridine derivatives enable N-terminal cysteine bioconjugation and peptide bond cleavage of glutathione under aqueous and mild conditions.RSC advances · 2024Article
- Solid-Phase Synthesis of Caged Luminescent Peptides via Side Chain Anchoring.Bioconjugate chemistry · 2023Article
- Leveraging Ligand Affinity and Properties: Discovery of Novel Benzamide-Type Cereblon Binders for the Design of PROTACs.Journal of medicinal chemistry · 2023Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.