Disease relevance of phenylboronic acid

• These techniques provided evidence for a two-step mechanism of binding of the first two boronic acids mentioned above to beta-lactamase I, and for benzeneboronic acid to a beta-lactamase from Pseudomonas aeruginosa [1].
• Direct isolation of subtilisin from a Bacillus subtilis cultural filtrate on phenylboronic acid-containing sorbent gives a virtually homogenous enzyme (42-fold purification) in a nearly-quantitative yield [2].
• Synthesis and in vitro evaluation of the phenylboric acid derivative entrapped lipiodol in boron neutron capture therapy for hepatoma [3].

High impact information on phenylboronic acid

• The activity of cholesterol esterase in the presence of compound 1 or 2 can be protected by the competitive inhibitor, phenylboronic acid [4].
• A multinuclear NMR study of the interaction between phenylboronic acid (PBA) and sialic acid (Neu5 Ac) has been performed [5].
• Affinity interactions between phenylboronic acid-carrying self-assembled monolayers and flavin adenine dinucleotide or horseradish peroxidase [6].
• A new purification procedure based on phenylboronic acid-agarose (PBA) affinity chromatography was developed to isolate CHIP28 [7].
• According to 1H correlation NMR spectroscopic studies performed in 80/20 (v/v) H2O/2H2O, no such resonance is found in native subtilisins (even at -2 degrees C and pH 6.0), but it is present in thiolsubtilisins and in the phenylboronic acid derivatives of the serine enzymes [8].

Biological context of phenylboronic acid

• A highly rigid dibenzo[a,d]cycloheptenyl dibenzophosphole with a pre-organized concave shaped binding site acts as an efficient ligand in the palladium catalyzed Suzuki-Miyaura coupling process between halogenoaromatics and phenylboronic acid [9].
• [reaction: see text] A phenylboronic acid derivative of a well-known dye (Lucifer yellow) recognizes L-DOPA through a combination of reversible esterification, charge transfer, and electrostatic interactions [10].
• Among the three phenylboronic acid derivatives, i.e. 4-(4, 5-diphenyl-1H-imidazol-2-yl)phenylboronic acid (DPA), 4-[4(or 5)-(4-dimethylaminophenyl)-5(or 4)-phenyl-1H-imidazol-2-yl]phenylboronic acid (DAPA) and 4-[4, 5-di(2-pyridyl)-1H-imidazol-2-yl]phenylboronic acid (DPPA), DPPA was found to be the most potent enhancer [11].
• A phenylboronic acid (PBA) derivatized Bond Elut column has been investigated for the selective purification of oligosaccharide alditols and of oligosaccharide derivatives formed by reductive amination reactions [12].
• The kinetics of inhibition of rice bran lipase (RBL) by phenylboronic acid (PBA) was studied to elucidate the nature of inhibition and the effect of the inhibitor on the structure-function of RBL [13].

Anatomical context of phenylboronic acid

• This suggests that proliferation of lymphocytes was induced through the binding of phenylboronic acid moiety in poly(AAm-co-PBA) with glycoproteins existing on the plasma membrane surface of lymphocytes [14].
• Effect of phenylboronic acid groups in copolymers on endothelial cell differentiation into capillary structures [15].

Associations of phenylboronic acid with other chemical compounds

• The system exploits bioconjugates with appended phenylboronic acid (PBA) moieties and a support-bound phenylboronic acid complexing reagent derived from salicylhydroxamic acid (SHA) for protein immobilization on a chromatographic support [16].
• Colloidal gold nanoparticles as catalyst for carbon-carbon bond formation: application to aerobic homocoupling of phenylboronic acid in water [17].
• Cyclic derivatives formed by reaction of sphingosines with methane-, n-butane- and benzeneboronic acid have been examined by gas-liquid chromatography (GLC) and by combined GLC-mass spectrometry (MS) [18].
• The effects of phenylboronic acid concentration, ionic strength, and buffer pH on the equilibrium hydrogel swelling were also studied [19].
• Amine effect on phenylboronic acid complex with glucose under physiological pH in aqueous solution [20].

Gene context of phenylboronic acid

• Excellent hCA IV inhibitory properties showed sulfamic acid, sulfamide, phenylboronic acid and phenylarsonic acid, with K(i)'s in the range of 0.87-0.93 microM, whereas their affinities for the other investigated isozymes were in the millimolar range [21].
• The urine was treated with beta-glucuronidase and sulfatase, and then the BaP-tetraols were enriched by reverse-phase and phenylboronic acid solid-phase extraction [22].
• The monomeric diphosphino Pd(II) complex 1 and the first three generations of dendritic analogues G1, G2, and G3 are efficient catalysts for the Suzuki coupling reaction of halogenoarenes, including chloroarenes with phenylboronic acid [23].
• [reaction: see text] Cyclopalladated compounds derived from the ortho-metalation of benzylic tert-butyl thioethers are excellent catalyst precursors for the Suzuki cross-coupling reaction of aryl bromides and chlorides with phenylboronic acid under mild reaction conditions [24].
• Lectin-like function was demonstrated in this study for a novel water-soluble polymer with phenylboronic acid residues (poly (AAPBA-DMAm)), which induced appreciable proliferation of murine spleen lymphocytes with an increased expression of interleukin-2 (IL-2) receptor on their surface [25].

Analytical, diagnostic and therapeutic context of phenylboronic acid

• Isoelectric-focusing of the haemoglobin fractions obtained from affinity chromatography indicate that, in addition to haemoglobin A1c, some haemoglobin A is also bound to immobilized phenylboronic acid [26].
• Separation of glycosylated haemoglobins using immobilized phenylboronic acid. Effect of ligand concentration, column operating conditions, and comparison with ion-exchange and isoelectric-focusing [26].
• Methoximation was carried out in urine samples which were subsequently applied to phenylboronic acid cartridges, reversed-phase cartridges and thin-layer chromatography [27].
• A column-switching HPLC method using an internal-surface phenylboronic acid precolumn for the selective extraction of beta-blockers from biological fluids has been developed [28].
• Selective extraction of beta-blockers from biological fluids by column-switching high-performance liquid chromatography using an internal-surface phenylboronic acid precolumn [28].

References