ArticleJournal of the American Chemical Society2016
Hydrogen Bonding of 1,2-Azaborines in the Binding Cavity of T4 Lysozyme Mutants: Structures and Thermodynamics.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
- Substituent-rebound skeletal editing for precise boron-to-carbon single-atom swapping.Nature communications · 2026Article
- Organocatalysed three-component modular synthesis of BN isosteres and BN-2,1-azaboranaphthalenes via Wolff-type rearrangement.Nature chemistry · 2026Article
- Synthesis of Chiral δ-Aminoboronic Esters by Enantioselective Hydrogenation of 1,2-Azaborines.Angewandte Chemie (International ed. in English) · 2025Article
- Alkali metal salts of 1,2,3-benzodiazaborines: platforms for late-stageChemical science · 2025Article
- Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres.Nature chemistry · 2024Article
- Advances in organocatalyzed synthesis of organic compounds.RSC advances · 2024Review
- Solvatochromic and Aggregation-Induced Emission Active Nitrophenyl-Substituted Pyrrolidinone-Fused-1,2-Azaborine with a Pre-Twisted Molecular Geometry.Journal of materials chemistry. C · 2023Article
- The aromatic Claisen rearrangement of a 1,2-azaborine.Organic & biomolecular chemistry · 2023Article
- Synthesis of BN-Polyarenes by a Mild Borylative Cyclization Cascade.Organic letters · 2022Article
- 1,10a-Dihydro-1-aza-10a-boraphenanthrene and 6a,7-Dihydro-7-aza-6a-boratetraphene: Two New Fluorescent BN-PAHs.The Journal of organic chemistry · 2021Article
- Flexible CDOCKER: Hybrid Searching Algorithm and Scoring Function with Side Chain Conformational Entropy.Journal of chemical information and modeling · 2021Article
- The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.Journal of the American Chemical Society · 2021Article
- Energy penalties enhance flexible receptor docking in a model cavity.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Temperature artifacts in protein structures bias ligand-binding predictions.Chemical science · 2021Article
- Rhodium-Mediated Stoichiometric Synthesis of Mono-, Bi-, and Bis-1,2-Azaborinines: 1-Rhoda-3,2-azaboroles as Reactive Precursors.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Selectivity in the Elaboration of Bicyclic Borazarenes.Advanced synthesis & catalysis · 2021Article
- Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes.Angewandte Chemie (International ed. in English) · 2020Article
- Cation-π binding ability of BN indole.Chemical communications (Cambridge, England) · 2020Article
- Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.Angewandte Chemie (International ed. in English) · 2019Article
- Exploring the strength of a hydrogen bond as a function of steric environment using 1,2-azaborine ligands and engineered T4 lysozyme receptors.Organic & biomolecular chemistry · 2019Article
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4 authors.
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Abstract
Protein crystallography and calorimetry were used to characterize the binding of 1,2-azaborines to model cavities in T4 lysozyme in direct comparison to their carbonaceous counterparts. In the apolar L99A cavity, affinity for Ab dropped only slightly versus benzene. In the cavity designed to accommodate a single hydrogen bond (L99A/M102Q), Gln102═O···H-N hydrogen bonding for Ab and BEtAb was observed in the crystallographic complexes. The strength of the hydrogen bonding was estimated as 0.94 and 0.64 kcal/mol for Ab and BEtAb, respectively. This work unambiguously demonstrates that 1,2-azaborines can be readily accommodated in classic aryl recognition pockets and establishes one of 1,2-azaborine's distinguishing features from its carbonaceous isostere benzene: its ability to serve as an NH hydrogen bond donor in a biological setting.
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