Boronic Acid‐Based Receptors

Fossey, John S.; James, Tony D.

doi:10.1002/9780470661345.smc072

Cited by 4 publications

(3 citation statements)

References 197 publications

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“…The co-authors of this report have investigated triazoles as chemosensors − and as products of asymmetric synthesis. − Furthermore, an interest in boronic acid derivatives as chemosensors, − including the use of cross-coupling reactions as a means of sensing, means the co-authors of this report are familiar with boronic acids and esters . As such, a desire to bring together these streams of research under one umbrella has led to the research reported in this manuscript.…”

Section: Introductionmentioning

confidence: 99%

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

et al. 2018

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Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. Bulky substrates were tested, and lead-like product formation was demonstrated. The online tool SambVca2.0 was used to assess steric parameters of ligands and preliminary buried volume determination using XRD-obtained data in a small number of cases proved to be informative. Two modeling approaches were compared for the determination of the buried volume of ligands where XRD data was not available. An approach with imposed steric restrictions was found to be superior in leading to buried volume determinations that closely correlate with observed reaction conversions. The online tool LLAMA was used to determine lead-likeness of potential Suzuki–Miyaura cross-coupling products, from which 10 of the most lead-like were successfully synthesized. Thus, confirming these readily accessible triazole-containing phosphines as highly suitable ligands for reaction screening and optimization in drug discovery campaigns.

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Section: Introductionmentioning

confidence: 99%

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

et al. 2018

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“…Alternatively, boronic acids, which are widely accepted as capture molecules for saccharides [ 68 ], can be modified to achieve a high selectivity for glucose binding. The geminal hydroxyl groups of boronic acids eagerly bind to the cis-diols of various sugar molecules; however, not specifically glucose.…”

Section: Diabetesmentioning

confidence: 99%

In Vitro and In Vivo SERS Biosensing for Disease Diagnosis

et al. 2018

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For many disease states, positive outcomes are directly linked to early diagnosis, where therapeutic intervention would be most effective. Recently, trends in disease diagnosis have focused on the development of label-free sensing techniques that are sensitive to low analyte concentrations found in the physiological environment. Surface-enhanced Raman spectroscopy (SERS) is a powerful vibrational spectroscopy that allows for label-free, highly sensitive, and selective detection of analytes through the amplification of localized electric fields on the surface of a plasmonic material when excited with monochromatic light. This results in enhancement of the Raman scattering signal, which allows for the detection of low concentration analytes, giving rise to the use of SERS as a diagnostic tool for disease. Here, we present a review of recent developments in the field of in vivo and in vitro SERS biosensing for a range of disease states including neurological disease, diabetes, cardiovascular disease, cancer, and viral disease.

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“…To enable Anticalins for the recognition of sugar ligands, and to overcome the camouflage effect in aqueous solution, we endeavored the incorporation of boronic acid, which is known to form reversible covalent complexes with cis -diols as they usually occur in saccharides and their derivatives . This type of functional group provides an ideal reagent for selective molecular recognition of sugars and has led to the development of boronic acid-based small-molecule sensors .…”

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Rational Design of an Anticalin-Type Sugar-Binding Protein Using a Genetically Encoded Boronate Side Chain

et al. 2017

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The molecular recognition of carbohydrates plays a fundamental role in many biological processes. However, the development of carbohydrate-binding reagents for biomedical research and use poses a challenge due to the generally poor affinity of proteins toward sugars in aqueous solution. Here, we describe the effective molecular recognition of pyranose monosaccharides (in particular, galactose and mannose) by a rationally designed protein receptor based on the human lipocalin scaffold (Anticalin). Complexation relies on reversible covalent cis-diol boronate diester formation with a genetically encoded l-boronophenylalanine (Bpa) residue which was incorporated as a non-natural amino acid at a sterically permissive position in the ligand pocket of the Anticalin, as confirmed by X-ray crystallography. Compared with the metal-ion and/or avidity-dependent oligovalent lectins that prevail in nature, our approach offers a novel and promising route to generate tight sugar-binding reagents both as research reagents and for biomedical applications.

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Boronic Acid‐Based Receptors

Cited by 4 publications

References 197 publications

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

In Vitro and In Vivo SERS Biosensing for Disease Diagnosis

Rational Design of an Anticalin-Type Sugar-Binding Protein Using a Genetically Encoded Boronate Side Chain

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