Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography
In High-Performance Liquid Chromatography (HPLC), the separation of reducing sugars can typically show three possible typologies of chromatographic profiles (i.e., single peak, two resolved peaks and two peaks interconnected by a plateau) due to the rate at which the relevant α/β anomers interconver...
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MDPI AG
2022-08-01
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| Series: | Separations |
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| Online Access: | https://www.mdpi.com/2297-8739/9/8/203 |
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| author | Andrea Calcaterra Simone Manetto Fabio Buonsenso Antonio Francioso Marco Pierini Claudio Villani |
| author_facet | Andrea Calcaterra Simone Manetto Fabio Buonsenso Antonio Francioso Marco Pierini Claudio Villani |
| author_sort | Andrea Calcaterra |
| collection | DOAJ |
| description | In High-Performance Liquid Chromatography (HPLC), the separation of reducing sugars can typically show three possible typologies of chromatographic profiles (i.e., single peak, two resolved peaks and two peaks interconnected by a plateau) due to the rate at which the relevant α/β anomers interconversion (anomerization) can take place in relation to their elution-time. By analyzing these chromatographic profiles, thermodynamic and kinetic properties of anomerization phenomenon can be extrapolated. In this work we studied the anomerization of some monosaccharides by using a recently developed photo-click cysteine-based stationary phase through dynamic hydrophilic interaction liquid chromatography (D-HILIC) conditions. In the 5–25 °C temperature range, the ΔG<sup>#</sup><sub>α→β</sub> and ΔG<sup>#</sup><sub>β→α</sub> barriers were found to achieve values within the interval 21.1/22.2 kcal/mol for glucose, with differences between α→β and β→α reactions of about 0.4 kcal/mol. For xylose, in the same temperature range, the ΔG<sup>#</sup><sub>α→β</sub> and ΔG<sup>#</sup><sub>β→α</sub> barriers are between 20.7 to 21.5 kcal/mol, with differences between α→β and β→α reactions of about 0.2 kcal/mol. The experimental data are in agreement with those reported in literature, confirming the this new stationary phase using HILIC conditions is a robust platform to measure kinetic and thermodynamic properties of the isomerization reaction. |
| first_indexed | 2024-03-09T03:50:46Z |
| format | Article |
| id | doaj.art-af4101b449ba44c5bf3e10c8b607cc22 |
| institution | Directory Open Access Journal |
| issn | 2297-8739 |
| language | English |
| last_indexed | 2024-03-09T03:50:46Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Separations |
| spelling | doaj.art-af4101b449ba44c5bf3e10c8b607cc222023-12-03T14:28:03ZengMDPI AGSeparations2297-87392022-08-019820310.3390/separations9080203Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid ChromatographyAndrea Calcaterra0Simone Manetto1Fabio Buonsenso2Antonio Francioso3Marco Pierini4Claudio Villani5Department of Chemistry and Drug Technology, Sapienza University of Rome, 00185 Rome, ItalyDepartment of Chemistry and Drug Technology, Sapienza University of Rome, 00185 Rome, ItalyDepartment of Chemistry and Drug Technology, Sapienza University of Rome, 00185 Rome, ItalyDepartment of Biological Chemistry, Sapienza University of Rome, 00185 Rome, ItalyDepartment of Chemistry and Drug Technology, Sapienza University of Rome, 00185 Rome, ItalyDepartment of Chemistry and Drug Technology, Sapienza University of Rome, 00185 Rome, ItalyIn High-Performance Liquid Chromatography (HPLC), the separation of reducing sugars can typically show three possible typologies of chromatographic profiles (i.e., single peak, two resolved peaks and two peaks interconnected by a plateau) due to the rate at which the relevant α/β anomers interconversion (anomerization) can take place in relation to their elution-time. By analyzing these chromatographic profiles, thermodynamic and kinetic properties of anomerization phenomenon can be extrapolated. In this work we studied the anomerization of some monosaccharides by using a recently developed photo-click cysteine-based stationary phase through dynamic hydrophilic interaction liquid chromatography (D-HILIC) conditions. In the 5–25 °C temperature range, the ΔG<sup>#</sup><sub>α→β</sub> and ΔG<sup>#</sup><sub>β→α</sub> barriers were found to achieve values within the interval 21.1/22.2 kcal/mol for glucose, with differences between α→β and β→α reactions of about 0.4 kcal/mol. For xylose, in the same temperature range, the ΔG<sup>#</sup><sub>α→β</sub> and ΔG<sup>#</sup><sub>β→α</sub> barriers are between 20.7 to 21.5 kcal/mol, with differences between α→β and β→α reactions of about 0.2 kcal/mol. The experimental data are in agreement with those reported in literature, confirming the this new stationary phase using HILIC conditions is a robust platform to measure kinetic and thermodynamic properties of the isomerization reaction.https://www.mdpi.com/2297-8739/9/8/203monosaccharide anomersD-HILICD-HPLCinterconversion energy barrierAuto-DHPLC-Y2KDCXplorer |
| spellingShingle | Andrea Calcaterra Simone Manetto Fabio Buonsenso Antonio Francioso Marco Pierini Claudio Villani Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography Separations monosaccharide anomers D-HILIC D-HPLC interconversion energy barrier Auto-DHPLC-Y2K DCXplorer |
| title | Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography |
| title_full | Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography |
| title_fullStr | Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography |
| title_full_unstemmed | Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography |
| title_short | Separation of Monosaccharide Anomers on Photo-Click Cysteine-Based Stationary Phase: The α/β Interconversion Process Studied by Dynamic Hydrophilic Liquid Chromatography |
| title_sort | separation of monosaccharide anomers on photo click cysteine based stationary phase the α β interconversion process studied by dynamic hydrophilic liquid chromatography |
| topic | monosaccharide anomers D-HILIC D-HPLC interconversion energy barrier Auto-DHPLC-Y2K DCXplorer |
| url | https://www.mdpi.com/2297-8739/9/8/203 |
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