ArticleOrganic & biomolecular chemistry2019
Biocompatible conjugation of Tris base to 2-acetyl and 2-formyl phenylboronic acid.
Article in Organic & biomolecular chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Dynamic Covalent Functionalization of DNA Origami via Iminoboronate Chemistry.Journal of the American Chemical Society · 2026Article
- Lan enzyme-free construction of lanthionine-bridged macrocyclic phage libraries.Chemical science · 2026Article
- Lysine-Targeted Reversible Covalent Ligand Discovery for Proteins via Phage Display.Journal of the American Chemical Society · 2022Article
- Boronic acid with high oxidative stability and utility in biological contexts.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Boronic acid based dynamic click chemistry: recent advances and emergent applications.Chemical science · 2020Review
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3 authors.
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Abstract
We describe the biocompatible conjugation of the Tris base to 2-formyl and 2-acetylphenylboronic acid (abbreviated as 2-FPBA and 2-APBA respectively), which have emerged as a versatile chemotype for fast biocompatible conjugation reactions. Tris base was found to react with 2-FPBA/APBA to give oxazolidinoboronate (OzB) complexes, analogous to the thiazolidinoboronate (TzB) and imidazolidinoboronate (IzB) complex formation that we recently reported. The Tris conjugations proceed well in complex biological media, and in contrast to the TzB/IzB complexes, the Tris conjugates exhibit superior kinetic stability (dissociation over days) as well as chemical stability against oxidation. We demonstrate the utility of such conjugation chemistries via a small molecule-induced peptide cyclization in blood serum.
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