The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears

Yan, Jun; Springsteen, Greg; Deeter, Susan; Wang, Binghe

doi:10.1016/j.tet.2004.08.051

Cited by 673 publications

(640 citation statements)

References 39 publications

Supporting

Mentioning

568

Contrasting

Unclassified

Order By: Relevance

“…The pKa for 3 (7.4 ± 0.1) and 6 (7.1 ± 0.1) is shifted by 1.4 and 1.7 pH units relative to that of phenylboronic acid (8.8 ± 0.1), respectively. This result is in consistent with the Hamment correlation between the pKa of substituted phenylboronic acid and its substituents [20]. The introduction of electron withdrawing groups such as sulfonyl and sulfonamide into the ring of phenylboronic acid substantially lowers the boronate pKa, as expected.…”

Section: Boronate Pka Of 3 Andsupporting

confidence: 89%

“…The pKa values of 4-(N-allylsulfamoyl)-phenylboronic acid 3 and 4-(3-butenesulfonyl)-phenylboronic acid 6 were measured by changes in the UV absorption following the titration of 1.0 mM of the respective boronic acid in 0.1 M phosphate buffer with 0.1 M NaOH [20]. A comparison of the two synthetic substituted phenylboronic acids with phenylboronic acid is displayed in Figure 1.…”

Section: Boronate Pka Of 3 Andmentioning

confidence: 99%

“…The result is probably related to the loading amount of boronic acid on silica. It should be noted that many other factors, such as the solubility of boronic acid and the nature of buffer, etc, could also affect the boronate-diol binding [20,22].…”

Section: Hplc Evaluation Of Boronate Affinitymentioning

confidence: 99%

“…Figure 4 and 5 show the chromatography of the three adenosine phosphates on our boronate affinity column at pH6.0 and the pH-dependent change in retention factors, respectively. Because alkyl cis-diols show much lower affinity towards boronic acids than aryl diols [20], the lower retention for alkyl cis-diols is expected compared to L-DOPA, (-)-norepinephrine and (-)-epinephrine. Based on the differences in adenosine phosphate retention, the number of negative charges on the analytes shows a significant influence on the association of analyte to the boronate ligand.…”

Section: Hplc Evaluation Of Boronate Affinitymentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH

Pennington

Stobaugh

et al. 2008

Analytical Biochemistry

View full text Add to dashboard Cite

Two new types of boronate affinity solid phases were synthesized and characterized. The materials were prepared by silylation of porous silica gel with monochlorosilane derivatives containing synthetic sulfonyl-and sulfonamide-substituted phenylboronic acids. The new solid phases were evaluated for boronate affinity chromatography with aryl and alkyl cis-diol compounds, and found suitable for the retention of cis-diols under acidic conditions. Significant correlations between the retention factor (K) and the pH of the mobile phase demonstrate that the binding of cis-diols to the solid phases is best rationalized by chelation. Based on the low ionization constant, caused by the electron-withdrawing effects of the sulfonyl and sulfonamide groups, these media display an enhanced affinity for cis-diols as compared to unsubstituted phenylboronic acid. Utilizing Isocratic elution, a mixture of various biologically relevant L-tyrosines, L-DOPA and several catecholamines were resolved with a mobile phase composed of 0.05 M, pH5.5 phosphate buffer. Mono-, di-and triphosphates of adenosine were also separated at pH 6.0. Hence, the new boronate solid phase offers efficient affinity separation and purification of cis-diol containg molecules under rather mild pH regions.

show abstract

Section: Boronate Pka Of 3 Andsupporting

confidence: 89%

Section: Boronate Pka Of 3 Andmentioning

confidence: 99%

Section: Hplc Evaluation Of Boronate Affinitymentioning

confidence: 99%

Section: Hplc Evaluation Of Boronate Affinitymentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH

Pennington

Stobaugh

et al. 2008

Analytical Biochemistry

View full text Add to dashboard Cite

show abstract

“…In fact, binding of cis-diols to boronic acids is not as simple as it appears (Yan et al, 2004). Boronic acids, as a result of their deficient valence (sp 2 hybridization state) contain an empty p orbital and adopt a trigonal, coplanar geometry.…”

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

View full text Add to dashboard Cite

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.

show abstract

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

2005

View full text Add to dashboard Cite

The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears

Cited by 673 publications

References 39 publications

Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH

Synthesis of sulfonamide- and sulfonyl-phenylboronic acid-modified silica phases for boronate affinity chromatography at physiological pH

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

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

Contact Info

Product

Resources

About