Solvent effects on acid-base behavior: Five uncharged acids in water-sulfolane solvents

Bates, Roger G.; Pawlak, Zenon

doi:10.1007/bf00654338

Cited by 14 publications

(5 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Overall, however, the ACS of Lyz and (Lyz + L1) complex in the presence and absence of sulfolane on liquid sample DESI spectra were lower than the ACS observed on their corresponding ESI spectra when the same solutions were sprayed. The lower ACS observed in the DESI spectra, which is consistent with the results of previous studies [58][59][60], may be due to the presence of ACN vapor in the source region. Acetonitrile has a higher gasphase basicity (178.8 kcal mol [31], is significant in that it reveals that protein supercharging and the reduction in the K a of the (Lyz + L1) complex caused by sulfolane are independent processes.…”

Section: Supercharging and Liquid Sample Desi-mssupporting

confidence: 91%

“…Consequently, it would seem that loss of affinity is related to a general solvent effect, whereby sulfolane increases the energetic penalty associated with solvent reorganization of the L1 and Lyz required for binding. That the addition of sulfolane to aqueous solutions affects the hydrogen bonding network of water provides indirect support for this hypothesis [58].…”

Section: Influence Of Sulfolane On the (Lyz + L1) Complex In Solutionmentioning

confidence: 99%

See 1 more Smart Citation

Influence of Sulfolane on ESI-MS Measurements of Protein–Ligand Affinities

Yao

Richards

Kitova

et al. 2015

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Abstract. The results of an investigation into the influence of sulfolane, a commonly used supercharging agent, on electrospray ionization mass spectrometry (ESI-MS) measurements of protein-ligand affinities are described. Binding measurements carried out on four protein-carbohydrate complexes, lysozyme with β-D-GlcNAc-revealed that sulfolane generally reduces the apparent (as measured by ESI-MS) protein-ligand affinities. To establish the origin of this effect, a detailed study was undertaken using the lysozyme-tetrasaccharide interaction as a model system. Measurements carried out using isothermal titration calorimetry (ITC), circular dichroism, and nuclear magnetic resonance spectroscopies reveal that sulfolane reduces the binding affinity in solution but does not cause any significant change in the higher order structure of lysozyme or to the intermolecular interactions. These observations confirm that changes to the structure of lysozyme in bulk solution are not responsible for the supercharging effect induced by sulfolane. Moreover, the agreement between the ESI-MS and ITC-derived affinities indicates that there is no dissociation of the complex during ESI or in the gas phase (i.e., in-source dissociation). This finding suggests that supercharging of lysozyme by sulfolane is not related to protein unfolding during the ESI process. Binding measurements performed using liquid sample desorption ESI-MS revealed that protein supercharging with sulfolane can be achieved without a reduction in affinity.

show abstract

Section: Supercharging and Liquid Sample Desi-mssupporting

confidence: 91%

Section: Influence Of Sulfolane On the (Lyz + L1) Complex In Solutionmentioning

confidence: 99%

Influence of Sulfolane on ESI-MS Measurements of Protein–Ligand Affinities

Yao

Richards

Kitova

et al. 2015

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

“…It should also be borne in mind that the structural changes lead to variations in autoprotolysis constants of solvents [11], which, in turn, affect the magnitudes of (acid + base) equilibrium constants in mixed solvents. A majority of authors determining acidity constants of weak acids in binary solvent mixtures have reported linear relationships between pK a s and mole fraction of organic solvent [12][13][14]. However, there are also reports on non-linear relationships between acidity constants and composition of the mixtures [15].…”

Section: Introductionmentioning

confidence: 93%

Potentiometric investigations of (acid+base) equilibria in (n-butylamine+acetic acid) systems in binary (acetone+cyclohexane) solvent mixtures

Czaja

Kozák

Makowski

et al. 2005

The Journal of Chemical Thermodynamics

View full text Add to dashboard Cite

“…The physical properties density (p), dielectric constant (D), and viscosity ( ) of sulfolane + water mixtures (5) are given in Table I. The molar conductance values (A (S cm2 mol"1)) as a function of concentration (c (mol dm"3)) In sulfolane at 30 II and III, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Although the behavior of electrolytes In sulfolane has been the subject of several conductance Investigations, there have been a few conductance studies in sulfolane + water mixtures (5)(6)(7). The purpose of the present work Is to study the be-havior of some potassium and tetraalkylammonlum salts for x = 0.2, 0.4, 0.6, 0.8, and 1.0 for x sulfolane + (1 -x) water through conductivity measurements.…”

mentioning

confidence: 98%

Conductance behavior of some potassium and tetraalkylammonium salts in sulfolane + water

Srivastava¹,

Desai²

1992

J. Chem. Eng. Data

View full text Add to dashboard Cite

The conductance behavior of potassium plcrate, salicylate, bromide, and Iodide as well as tetraethylammonlum bromide and tetrabutylammonlum tetraphenylboride and Iodide has been studied at x = 0.20, 0.40, 0.60, and 0.80 (at 25 °C) and 1.0 (at 30 °C) for mixtures of x sulfolane + (1 -x) water. The conductance data are organized and treated on the basis of the Fuoss (1978) equation using the Fuoss computer program. Values of the limiting molar conductance (A,), association constant (AfA), and cosphere diameter (j?) are obtained as a result of the treatment. The limiting Ionic mobilities of the Individual Ions have been reported on the basis of tetrabutylammonlum tetraphenylboride reference electrolyte. The Walden product for each system Interestingly showed maxima and minima at different mole fractions of sulfolane studied.

show abstract

Solvent effects on acid-base behavior: Five uncharged acids in water-sulfolane solvents

Cited by 14 publications

References 23 publications

Influence of Sulfolane on ESI-MS Measurements of Protein–Ligand Affinities

Influence of Sulfolane on ESI-MS Measurements of Protein–Ligand Affinities

Potentiometric investigations of (acid+base) equilibria in (n-butylamine+acetic acid) systems in binary (acetone+cyclohexane) solvent mixtures

Conductance behavior of some potassium and tetraalkylammonium salts in sulfolane + water

Contact Info

Product

Resources

About