ArticleChemical science2016
The third orthogonal dynamic covalent bond.
Article in Chemical science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 69 citations in OpenAlex.
- Dual-Dynamic Covalently Cross-Linked Polyglycerol Hydrogels for Tumor Spheroid Culture.Biomacromolecules · 2025Article
- An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Dynamic Nucleophilic Aromatic Substitution of Tetrazines.Angewandte Chemie (International ed. in English) · 2021Article
- Simultaneous Formation of a Fully Organic Triply Dynamic Combinatorial Library.Organic letters · 2021Article
- A Giant [8+12] Boronic Ester Cage with 48 Terminal Alkene Units in the Periphery for Postsynthetic Alkene Metathesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Simultaneous CONature chemistry · 2020Article
- Engineering multilayer chemical networks.Chemical science · 2019Article
- A tetrahedral molecular cage with a responsive vertex.Chemical science · 2019Article
- Unravelling mechanistic features of organocatalysis with in situ modifications at the secondary sphere.Nature chemistry · 2019Article
- Tunable Orthogonal Reversible Covalent (TORC) Bonds: Dynamic Chemical Control over Molecular Assembly.Angewandte Chemie (International ed. in English) · 2019Review
- Dynamic self-correcting nucleophilic aromatic substitution.Nature chemistry · 2018Article
- Adaptable Fast Relaxing Boronate-Based Hydrogels for Probing Cell-Matrix Interactions.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2018Article
- Injectable dynamic covalent hydrogels of boronic acid polymers cross-linked by bioactive plant-derived polyphenols.Biomaterials science · 2018Article
- Redox Control over Acyl Hydrazone Photoswitches.Journal of the American Chemical Society · 2017Article
- Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.Chemical reviews · 2017Review
- Antiparallel Dynamic Covalent Chemistries.Journal of the American Chemical Society · 2017Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Orthogonal dynamic covalent bonds are of interest for the construction of functional systems. The orthogonality of disulfide and hydrazone exchange under basic and acidic conditions, respectively, is well established. However, the integration of boronate esters as the third bond has failed so far because they exchanged too easily, especially under hydrazone exchange conditions. In this report, a collection of bioinspired catechols derived from adhesive natural products from cyanobacteria is screened with phenylboronic acids with proximal alcohols (benzoboroxoles), amines and fluorines to identify the least labile boronate esters. Moreover, Kool's 2-aminophenol catalysts are introduced to selectively accelerate hydrazone exchange without disturbing sufficiently inert boronate esters. Based on these results, we identified three different conditions to selectively exchange disulfides, hydrazones and boronate esters, that is to demonstrate the existence of three orthogonal dynamic covalent bonds. Moreover, their compatibility with functional systems is confirmed by successful hydrazone exchange in multicomponent surface architectures in the presence of intact boronate esters and disulfides.
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Registered trials
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.