ArticleChemical communications (Cambridge, England)2015
Rapid formation of a stable boron-nitrogen heterocycle in dilute, neutral aqueous solution for bioorthogonal coupling reactions.
Article in Chemical communications (Cambridge, England), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
25 citing papers in PubMed.
- Dynamic Covalent Functionalization of DNA Origami via Iminoboronate Chemistry.Journal of the American Chemical Society · 2026Article
- Fluorescent Probes for Aldehyde Detection in Biological Systems: Design Principles, Spectroscopy, and Emerging Applications.Sensors (Basel, Switzerland) · 2026Review
- Designing Functional and Responsive Molecules with Boronic Acids.Accounts of chemical research · 2025Article
- Click processes orthogonal to CuAAC and SuFEx forge selectively modifiable fluorescent linkers.Nature chemistry · 2024Article
- The linkage-type and the exchange molecule affect the protein-labeling efficiency of iminoboronate probes.Organic & biomolecular chemistry · 2023Article
- Therapeutic Oligonucleotides: An Outlook on Chemical Strategies to Improve Endosomal Trafficking.Cells · 2023Review
- Insight intoChemical science · 2022Article
- Inhibiting C-4 Methyl Sterol Oxidase with Novel Diazaborines to Target Fungal Plant Pathogens.ACS chemical biology · 2022Article
- Iminoboronates as Dual-Purpose Linkers in Chemical Probe Development.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Boronic acid based dynamic click chemistry: recent advances and emergent applications.Chemical science · 2020Review
- Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.Journal of the American Chemical Society · 2020Article
- Click Chemistry Conjugations.Methods in molecular biology (Clifton, N.J.) · 2020Article
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- β-Hydroxy-Stabilized Boron-Nitrogen Heterocycles Enable Rapid and Efficient C-Terminal Protein Modification.Bioconjugate chemistry · 2019Article
- Site-Specific Bioconjugation and Multi-Bioorthogonal Labeling via Rapid Formation of a Boron-Nitrogen Heterocycle.Bioconjugate chemistry · 2019Article
- Versatile Bioconjugation Chemistries of ortho-Boronyl Aryl Ketones and Aldehydes.Accounts of chemical research · 2018Article
- Diazaborines as New Inhibitors of Human Neutrophil Elastase.ACS omega · 2018Article
- Dynamic Formation of Imidazolidino Boronate Enables Design of Cysteine-Responsive Peptides.Organic letters · 2018Article
- Development and Elucidation of a Novel Fluorescent Boron-Sensor for the Analysis of Boronic Acid-Containing Compounds.Sensors (Basel, Switzerland) · 2017Article
- Borylated oximes: versatile building blocks for organic synthesis.Chemical communications (Cambridge, England) · 2017Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
Abstract
Combining 2-formylphenylboronic acid with 4-hydrazinylbenzoic acid in neutral aqueous solution at low, equimolar concentrations of the reagents results in a single, stable product, a 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine, in a matter of minutes with no side products. Application of this reaction to protein conjugation demonstrates that the reaction is orthogonal to protein functional groups, and the resulting conjugate withstands SDS-PAGE analysis. This reaction should be particularly useful for couplings that must be performed with low concentrations of reagents under physiologically compatible conditions.
Indexed as
Identifiers
What OpenQuestion holds
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.