Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications

Hall, Dennis G.

doi:10.1002/3527606548.ch1

Cited by 193 publications

(235 citation statements)

References 721 publications

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“…The boronic acid functional group in general has low toxicity [4,13,27]. However, when this group is accommodated into a larger molecule, the resulting compound may have effects specific to that structure which can cause cytotoxicity.…”

Section: Toxicitymentioning

confidence: 99%

“…Although boric acid (B(OH) 3 ) is used in insecticides and herbicide, it has low toxicity in humans, with lethal doses comparable to that of sodium chloride, common table salt (B(OH) 3 : LD 50 =2660 mg/kg; NaCl: LD 50 =3,000 mg/kg) [7,78]. Deboronation can occur by a number of routes, the main ones being metal-catalysed hydrolytic cleavage [27,48] and oxidative deboronation carried out by enzymes including cytochrome P450 [40,44,59]. Boric acid is then excreted by the kidneys without further metabolism [57].…”

Section: Toxicitymentioning

confidence: 99%

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Molecular recognition with boronic acids—applications in chemical biology

2013

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Small molecules have long been used for the selective recognition of a wide range of analytes. The ability of these chemical receptors to recognise and bind to specific targets mimics certain biological processes (such as proteinsubstrate interactions) and has therefore attracted recent interest. Due to the abundance of biological molecules possessing polyhydroxy motifs, boronic acids-which form fivemembered boronate esters with diols-have become increasingly popular in the synthesis of small chemical receptors. Their targets include biological materials and natural products including phosphatidylinositol bisphosphate, saccharides and polysaccharides, nucleic acids, metal ions and the neurotransmitter dopamine. This review will focus on the many ways in which small chemical receptors based on boronic acids have been used as biochemical tools for various purposes, including sensing and detection of analytes, interference in signalling pathways, enzyme inhibition and cell delivery systems. The most recent developments in each area will be highlighted.

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Section: Toxicitymentioning

confidence: 99%

Section: Toxicitymentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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“…Boronic acids, as a result of their deficient valence (sp 2 hybridization state) contain an empty p orbital and adopt a trigonal, coplanar geometry. At neutral and acidic pH values, they are able to interact by charge transfer interactions with Lewis bases, such as the amino groups typically found in proteins (Hall, 2005). However, at alkaline pH values (namely 8.5), the trigonal boronic acid group ionizes to form a tetrahedral hydroxyboronate anion.…”

Section: Selectivity Studiesmentioning

confidence: 99%

Capture of human monoclonal antibodies from a clarified cell culture supernatant by phenyl boronate chromatography

Azevedo

Gomes

Borlido

et al. 2010

J of Molecular Recognition

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In this work, we investigated the feasibility of using phenyl boronate (PB) chromatography for the direct capture of monoclonal antibodies from a CHO cell supernatant. Preliminary results, using pure protein solutions have shown that PB media can bind to human antibodies, not only at strong alkaline conditions but also at acidic pH values. In fact, antibodies have been found to bind in the pH range 5.5-8.5. On the other hand, insulin and human serum albumin did not bind at alkaline pH but at lower pH, which reflects the importance of non-specific interactions with the matrix. Different binding and eluting buffers were evaluated for the capture of immunoglobulin G (IgG) from a CHO cell supernatant and the most promising results were obtained using 20 mM 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid at pH 8.5 as binding buffer and 1.5 M Tris-HCl as eluting buffer. Using a step elution, all IgG was recovered in the elution pool with a maximum purification factor of 56. A gradient elution allowed a further increase of the final purity, yet achieving a slightly lower yield. IgG recovery was around 85% and the purification factor was 76. The highest purity was obtained when the pH of the cell supernatant feed was previously adjusted to 8.5. Starting from an initial protein purity of 1.1% and high-performance liquid chromatography (HPLC) purity of 2.2%, after PB adsorption, a final protein purity of 85% and a HPLC purity of 88% was achieved.

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“…corresponding esters [17]. Such esters are usually significantly less polar and they are consequently more volatile.…”

Section: A C I D H a V E A D I S T I N C T A F F I N I T Y T O A L C mentioning

confidence: 99%

Characterization of medium-temperature Sasol–Lurgi gasifier coal tar pitch

Papole

Focke

Manyala

2012

Fuel

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Medium-temperature gasifier pitch (MTP) is only partly soluble in acetonitrile, methanol and ethanol. Single-stage pitch extraction with a large quantity of methanol yielded two liquid phases containing 76 wt. % and 27 wt. % pitch respectively. The pitch fractions recovered from these two phases featured similar aromaticity indices. However, the pitch from the pitch-rich phase had a higher average molar mass and gave an improved carbon yield at 1000°C. Analysis of the methanol-insoluble pitch fraction showed that methanol extraction at reflux temperatures effectively removed boronic acid model compounds from pitch samples spiked with the same.

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Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications

Cited by 193 publications

References 721 publications

Molecular recognition with boronic acids—applications in chemical biology

Molecular recognition with boronic acids—applications in chemical biology

Capture of human monoclonal antibodies from a clarified cell culture supernatant by phenyl boronate chromatography

Characterization of medium-temperature Sasol–Lurgi gasifier coal tar pitch

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