Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution

2011 ◽  
Vol 64 (11) ◽  
pp. 1466 ◽  
Author(s):  
Michael G. Chudzinski ◽  
Yuechuan Chi ◽  
Mark S. Taylor
Keyword(s):  
Aqueous Solution ◽  
Boronic Acid ◽  
Covalent Binding ◽  
Boronic Acids ◽  
Association Constants ◽  
Electronic Tuning ◽  
Displacement Assay ◽  
High Level ◽  
Related Compounds ◽  
Borinic Acid

Association constants between diphenylborinic acid and representative analytes capable of reversible two-point covalent binding (diols, catechols, and hydroxy acids) were determined using an indicator-displacement assay. Unlike boronic acids, which have been studied in great detail as receptors for diols and related compounds, borinic acids have effectively been ignored as candidates for such applications. The results of this study indicate that diphenylborinic acid displays high affinity for certain analytes of this type in aqueous solution. Of particular interest are differences between the selectivity of the borinic acid and that of a boronic acid of similar pKa towards the series of analytes studied: the borinic acid displays an unusually high level of discrimination for catechols over carbohydrates. The distinct selectivity observed, and the unique opportunities for steric and electronic tuning of diarylborinic acids, suggest that these compounds hold significant potential for applications in aqueous-phase molecular recognition.

scholarly journals Recent development of boronic acid-based fluorescent sensors

RSC Advances ◽  
2018 ◽  
Vol 8 (51) ◽  
pp. 29400-29427 ◽  
Author(s):  
Guiqian Fang ◽  
Hao Wang ◽  
Zhancun Bian ◽  
Jie Sun ◽  
Aiqin Liu ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Boronic Acid ◽  
Lewis Acids ◽  
Boronic Acids ◽  
Fluorescent Sensors ◽  
Cyclic Esters

As Lewis acids, boronic acids can bind with 1,2- or 1,3-diols in aqueous solution reversibly and covalently to form five or six cyclic esters, thus resulting in significant fluorescence changes.

The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-L-phenylalanine and their Affinity for Alizarin

2007 ◽  
Vol 60 (11) ◽  
pp. 829 ◽  
Author(s):  
Peter J. Duggan ◽  
Daniel A. Offermann
Keyword(s):  
Peptide Synthesis ◽  
Boronic Acid ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Boronic Acids ◽  
Association Constants ◽  
Synthesis Methods ◽  
Selective Binding ◽  
Binding Characteristics ◽  
Potential Use

A library of solid-supported pentapeptide diboronic acids, a ‘lysine series’ and an ‘arginine series’, has been efficiently prepared using N-Fmoc-4-pinacolatoborono-l-phenylalanine and standard solid phase peptide synthesis methods. A technique for measuring the affinity of the chromophoric diol, alizarin, to the solid-supported peptide boronic acids has been developed. Considerable variation in alizarin binding strengths, both within and between arginine and lysine series was observed, with association constants in the range 200–1100 M–1 being recorded. The selective binding characteristics of these boronic acid–peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

Non-covalent functionalization of carbon nanotubes with boronic acids for the wiring of glycosylated redox enzymes in oxygen-reducing biocathodes

2014 ◽  
Vol 2 (16) ◽  
pp. 2228-2232 ◽  
Author(s):  
Bertrand Reuillard ◽  
Alan Le Goff ◽  
Michael Holzinger ◽  
Serge Cosnier
Keyword(s):  
Carbon Nanotubes ◽  
Carbon Nanotube ◽  
Boronic Acid ◽  
Covalent Binding ◽  
Boronic Acids ◽  
Redox Enzymes ◽  
Covalent Functionalization ◽  
Functionalization Of Carbon Nanotubes ◽  
Electrical Wiring ◽  
Boronic Acid Derivatives

Easy covalent binding and efficient electrical wiring of enzymes onto carbon nanotube deposits by pyrene-boronic acid derivatives.

Synthesis and properties of water-soluble porphyrins bearing multidentate ligands

2004 ◽  
Vol 08 (08) ◽  
pp. 1047-1054 ◽  
Author(s):  
Yoshio Uemori ◽  
Masato Sakurai ◽  
Atsuko Osada ◽  
Hiroki Munakata ◽  
Hiroyasu Imai ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Aromatic Compounds ◽  
Covalent Binding ◽  
Nitrilotriacetic Acid ◽  
Association Constants ◽  
Water Soluble ◽  
Para Position ◽  
Multidentate Ligands ◽  
Acid Base ◽  
Base Properties

Water-soluble porphyrins bearing multidentate ligands were prepared by covalent binding of nitrilotriacetic acid to 5,10,15,20-tetrakis(4-aminophenyl)porphyrin or three atropisomers of 5,10,15,20-tetrakis(2-aminophenyl)porphyrin. The acid-base properties and monomer-dimer behavior of the porphyrins were affected by the positions of the multidentate ligands with respect to the porphyrin plane. Among the porphyrins, the porphyrin bearing multidentate ligands at the para position of the phenyl groups dimerized in an aqueous solution. The association constants of the porphyrins with various aromatic compounds were studied in water at pH 7.4 containing 10 mM HEPES at 25°C. These values varied with the structure and charges of both the porphyrins and the aromatic compounds. The association constants of the porphyrin bearing multidentate ligands at the 2-position of the phenyl groups were small compared to those of the porphyrin bearing multidentate ligands at the 4-position.

Enantioselective Recognition of Chiral Guests by the Water-Soluble Chiral Keplerate {Mo132} Spherical Capsule with 30 Inner Lactate Ligands

2019 ◽  
Author(s):  
Nancy Watfa ◽  
Weimin Xuan ◽  
Zoe Sinclair ◽  
Robert Pow ◽  
Yousef Abul-Haija ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Chiral Recognition ◽  
Association Constants ◽  
Water Soluble ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Dosy Nmr ◽  
Spherical Capsule ◽  
Surface Pores ◽  
Guest Chemistry

Investigations of chiral host guest chemistry are important to explore recognition in confined environments. Here, by synthesizing water-soluble chiral porous nanocapsule based on the inorganic metal-oxo Keplerate-type cluster, {Mo<sub>132</sub>} with chiral lactate ligands with the composition [Mo<sub>132</sub>O<sub>372</sub>(H<sub>2</sub>O)<sub>72</sub>(<i>x-</i>Lactate)<sub>30</sub>]<sup>42-</sup> (<i>x</i> = D or L), it was possible to study the interaction with a chiral guest, L/D-carnitine and (<i>R</i>/<i>S</i>)-2-butanol in aqueous solution. The enantioselective recognition was studied by quantitative <sup>1</sup>H NMR and <sup>1</sup>H DOSY NMR which highlighted that the chiral recognition is regulated by two distinct sites. Differences in the association constants (K) of L- and D-carnitine, which, due to their charge, are generally restricted from entering the interior of the host, are observed, indicating that their recognition predominantly occurs at the surface pores of the structure. Conversely, a larger difference in association constants (K<i><sub>S</sub></i>/K<i><sub>R</sub></i> = 3) is observed for recognition within the capsule interior of (<i>R</i>)- and (<i>S</i>)-2-butanol.

Effects of Aging on the Solubility of Palladium

1995 ◽  
Vol 412 ◽  
Author(s):  
C. Oda ◽  
H. Yoshikawa ◽  
M. Yui
Keyword(s):  
Aqueous Solution ◽  
Aging Time ◽  
Room Temperature ◽  
High Level Waste ◽  
Anaerobic Conditions ◽  
Dilute Aqueous Solution ◽  
Waste Repository ◽  
Ph Range ◽  
Effects Of Aging ◽  
High Level

AbstractPalladium solubility was measured in a dilute aqueous solution at room temperature in the pH range from 3 to 13 under anaerobic conditions. Crystalline Pd metal was clearly visible and the concentration of palladium in solution decreased gradually with aging time. The palladium concentrations in solution were less than 9.4×10-10M in the pH range from 4 to 10 and increased to 10-7M in the pH range greater than 10. This study suggests that palladium concentrations in certain high-level waste repository environments may be limited by Pd metal and may be less than 10-9M.

scholarly journals The binding of human complement proteins C5, factor B, β1H and properdin to complement fragment C3b on zymosan

1981 ◽  
Vol 199 (3) ◽  
pp. 485-496 ◽  
Author(s):  
R G DiScipio
Keyword(s):  
Protein Modification ◽  
Alternative Pathway ◽  
Covalent Binding ◽  
Association Constants ◽  
Affinity Constant ◽  
Distinct Region ◽  
Binding Studies ◽  
Factor B ◽  
Complement Proteins ◽  
Competition Binding

The covalent binding of complement fragment C3b to zymosan by the action of the alternative-pathway C3 convertase and the reversible binding of several complement proteins (component C5, factor B, beta 1H and properdin) to C3b on zymosan have been investigated. When C3b is deposited on zymosan after activation by a surface-bound C3 convertase, the C3b molecules are deposited in foci around the C3 convertase site, with an average of 30 C3b molecules per site. The association constants of C5, factor B, beta 1H, and properdin for C3b bound to zymosan have been determined. The association constants ranged from 6.5 x 10(-5) M-1 for factor B to 2.9 x 10(7) M-1 for properdin. An approximate stoichiometry of 1 : 1 for C5, factor B, and properdin binding to C3b has been observed. Curvilinear Scatchard plots were observed for beta 1H binding to C3b, with the maximal extrapolated ratio of beta 1H to C3b of 0.32. Physiological amounts of properdin increase by 7-fold the affinity constant for factor B binding to C3b with no alteration in the stoichiometry. Similarly, physiological amounts of factor B increase the affinity constant of properdin to C3b about 4-fold with only a small measured difference in stoichiometry. Competition binding studies and protein modification suggest that C5, factor B, beta 1H, and properdin each bind to a distinct region on C3b.

scholarly journals A Theoretical Model to Study the Interaction Between Boronic Acids and Insulin

2020 ◽  
Author(s):  
Durgesh Kumar ◽  
Kamlesh Kumari ◽  
PRASHANT SINGH
Keyword(s):  
Amino Acids ◽  
Theoretical Model ◽  
Boronic Acid ◽  
Significant Interaction ◽  
Biological Activities ◽  
Boronic Acids ◽  
Biological Molecules ◽  
Computational Tools ◽  
Medical Expertise ◽  
Stabilizing Agents

Boronic acids are widely used in various applications in view of their ability to recognize and bind at specific sites of the biological molecules to mimic several processes. Therefore, this has attracted the researchers, academician and medical expertise to explore them. In the present work, the authors have designed a theoretical approach to study the interaction of boronic acid with insulin using computational tools. A library of boronic acids (114 compounds) are designed, optimized and interacted with insulin using computational tools i.e. iGEMDOCK. Further, their different biological activities and toxicity are determined. Results indicates the promising potential of the boronic acids on interaction with the insulin. Amongst, 114 molecules of boronic acids, 3-Benzyloxyphenylboronic acid (71) showed the best interaction with amino-acids of insulin and significant interaction was shown with the Glu21 and His5 residues. Further, these results were compared with the stabilizing agents and found to be more potent.

(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki–Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 799-804 ◽  
Author(s):  
Mark Stradiotto ◽  
Ryan Sawatzky
Keyword(s):  
Boronic Acid ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Mild Conditions

The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki–Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described.

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