<div><div>Protons play a central role in many chemical reactions in living organisms. In some cases, a proton may be shared between two nearby molecular groups rather than being localized on just one. This phenomenon can strongly influence the properties and reactivity of biomolecules and is important for enzyme function.</div></div><div>Researchers led by Hanns Christian Schewe (IOCB Prague and Heyrovský Institute of the CAS) together with Lukáš Tomaník (UCT Prague and Fritz Haber Institute of the Max Planck Society) have now investigated proton sharing in a range of biologically relevant polycarboxylic acids dissolved in water, including several molecules related to the citric acid cycle (Krebs cycle).Using liquid-jet X-ray photoelectron spectroscopy (LJ-PES), a technique that reveals the chemical environment of atoms in molecules dissolved in water, the team was able to probe the position of protons on an ultrafast time scale. Unlike techniques such as NMR, which provide a time-averaged picture, photoelectron spectroscopy captures the instantaneous distribution of protons and can therefore distinguish more directly between localized and shared states.The results showed significant proton sharing only in maleic acid dissolved in water. In contrast, protons remained mostly localized at individual carboxylic groups in succinic acid, fumaric acid, malic acid, glutaric acid and citric acid. This suggests that proton sharing is not a common feature of these molecules when they are freely dissolved in water.<img src="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/IOCB_Prague_Cropped_part_of_the_cover_by_Schewe_et_al_with_the_use_of_Nano_Banana_2_0_2_2a408dbeb5.webp" alt="IOCB Prague: Cropped part of the cover by Schewe et al. with the use of Nano Banana 2.0: Full cover by Schewe et al. with the use of Nano Banana 2.0." srcset="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/thumbnail_IOCB_Prague_Cropped_part_of_the_cover_by_Schewe_et_al_with_the_use_of_Nano_Banana_2_0_2_2a408dbeb5.webp 117w," sizes="100vw" width="1620" height="2154">The difference appears to be largely controlled by molecular geometry. In maleic acid, the two carboxylic groups are held close together, creating favorable conditions for proton sharing. More flexible molecules can adopt conformations in which the groups are farther apart, while water molecules form strong hydrogen bonds with them and favor localized protons.However, the situation may be different inside proteins. When a carboxylic acid binds in the active site of an enzyme, its shape and position can be tightly constrained. Such an environment could bring the relevant groups close enough together to promote proton sharing and thereby influence enzymatic reactions.The study highlights an important distinction: proton sharing may be rare in freely hydrated molecules but could become important when biomolecules are held in the right geometry by enzymes. It also demonstrates that LJ-PES is a powerful tool for studying proton behavior in solutions. Its ultrafast and site-specific sensitivity could in future help researchers investigate proton sharing directly in more complex chemical and biological systems.<blockquote><h4>The original article</h4><h4><a target="_blank" rel="noopener noreferrer" href="https://pubs.acs.org/jaaucr/article/6/6/3349/5084661/Proton-Sharing-in-Polycarboxylic-Acids-in-Aqueous">Proton Sharing in Polycarboxylic Acids in Aqueous Solution</a></h4>Lukáš Tomaník, Jiří Tůma, Gunnar Öhrwall, Ronny Golnak, Ngoc Lan Le Nguyen, Bruno Credidio, Harmanjot Kaur, Petr Slavíček, Bernd Winter, H. Christian Schewe<div>JACS Au, 2026, 6, 3349–3355</div><a target="_blank" rel="noopener noreferrer" href="https://doi.org/10.1021/jacsau.6c00377">https://doi.org/10.1021/jacsau.6c00377</a><h6>licenced under <a target="_blank" rel="noopener noreferrer" href="https://creativecommons.org/licenses/by/4.0/">CC-BY 4.0</a></h6></blockquote><h4>Abstract</h4>We investigate proton sharing in biologically relevant polycarboxylic acids in aqueous solutions using liquid-jet X-ray photoelectron spectroscopy. In contrast to techniques that record time-averaged proton positions, like nuclear magnetic resonance, photoelectron spectroscopy captures instantaneous proton distribution due to its ultrafast probing time scale. The method is, therefore, uniquely sensitive to the occurrence of proton sharing in an aqueous environment, as demonstrated here. We only observe significant proton sharing dynamics in maleic acid, where its monoanionic form shows a single, delocalized peak in the carbon 1s spectrum. Conversely, succinic acid, fumaric acid, malic acid, glutaric acid, and citric acid exhibit distinct peaks corresponding to separate, localized COOH and COO– groups, instead of shared protons. Our results reveal that intramolecular proton sharing in water is rather an exception for most biologically relevant polycarboxylic acids. This highlights the importance of enzyme-driven structural changes of polycarboxylic acids associated with proton sharing during metabolic processes.</div>

Proton sharing in polycarboxylic acids in aqueous solution

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Breathomics, Asthma & GC×GC: PH Stefanuto on Fighting the “Proof‑of‑Concept” Trap

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The Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences (IOCB Prague) is a leading scientific institution in the Czech Republic, recognized internationally. Its primary mission is basic research in the fields of chemical biology and medicinal chemistry, organic and material oriented chemistry, chemistry of natural compounds, biochemistry and molecular biology, physical chemistry, theoretical chemistry, and analytical chemistry. 

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KNAUER Eurospher II 100 Diol (U)HPLC Columns for NP (USP L20)

Diol packing material can be universally used in different polar modes (NP, RP and HILIC). Diol bonded phases are a versatile alternative to unbonded silica for normal phase separations.

Diol columns for Normal Phase in HPLC and UHPLC (USP L20)Diol packing material can be universally used in different polar modes (NP, RP and HILIC). Diol bonded phases are a versatile alternative to unbonded silica for normal phase separations with shorter equilibration times.The hydroxyl groups provide good selectivity without excessive retention, caused by the weaker H-bonding of the diol layer than of silanols. Some diol bonded phases have been developed specifically for applications in the HILIC mode.<h5>Properties</h5><ul><li>Separation mechanism: Hydrophilic interaction</li><li>Ultra pure, spherical high performance HPLC phase based on silica gel</li><li>Diol, no endcapping, with 5 % carbon content&nbsp;</li></ul><h5>Key features</h5><ul><li>High-class HPLC phase perfectly suited to take on routine analyses as well as the most ambitious chromatography tasks, classical Diol phase without endcapping and 5 % carbon content, outstanding mechanical and chemical stability.</li></ul><h5>Recommended application areas</h5><ul><li>Alternative to the silica packing with shorter equilibration time and comparable selectivity; due to the lower activity of these packings it can be also used for SEC-applications.</li></ul><img src="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/KNAUER_Diol_26fe64c2b9.webp" alt="KNAUER: Diol" srcset="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/thumbnail_KNAUER_Diol_26fe64c2b9.webp 156w," sizes="100vw" width="426" height="425"><blockquote>Tip: The most important column parameters for evaluation are retention time, peak symmetry and theoretical plates. Retention time to prove the reproducibility of measurements. Peak symmetry to estimate how good the column bed is packed (peak symmetry value of 1.0 is optimal). Theoretical plate numbers to determine the effectiveness of the HPLC column.</blockquote>Stationary phase Eurospher II 100 Diol is provided in these column types: analytical, semi-preparative and preparative.Eurospher II 100 Diol Analytical Columns are available with these parameters:<ul><li>Column length (mm): 50, 100, 150, 250</li><li>Column ID (mm): 3, 4, 4.6</li><li>Particle size (µm): 3, 5</li></ul>Eurospher II 100 Diol Semi-Preparative Standard Columns are available with these parameters:<ul><li>Column length (mm): 30, 50, 125, 150, 250</li><li>Column ID (mm): 8, 16</li><li>Particle size (µm): 5, 10</li></ul><h3>KNAUER (U)HPLC Columns</h3>Widest range of HPLC and UHPLC columns for all separation modes and applications.<ul><li>Safe Investment: Robust and reliable columns for attractive price&nbsp;</li><li>Separation Mode: Reversed Phase, HILIC, Normale</li><li>Simplicity: Easy purchase via our online store with fast delivery</li><li>Application: All-rounder for research or highly specialised for high-throughput analysis? We have the best column for your requirements.</li><li>Flexibility: Wide selection of column and particle sizes, for (U)HPLC applications up to 1000 bar</li></ul>KNAUER offers the perfect column for any small molecule separation. No matter which separation mode, molecule and the mobile phase, we offer a suitable (U)HPLC stationary phase. Choose from a wide range of modifications, particle sizes and column dimensions to suit your application. To elongate the lifetime of your column, you can choose to use a suitable precolumn.<img src="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/KNAUER_KNAUER_U_HPLC_C8_and_C8_A_Columns_083c60f401.webp" alt="KNAUER: KNAUER (U)HPLC Columns" srcset="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/thumbnail_KNAUER_KNAUER_U_HPLC_C8_and_C8_A_Columns_083c60f401.webp 182w," sizes="100vw" width="787" height="674">

KNAUER Eurospher II 100 Diol Prep HPLC Columns (USP L20)

Diol columns for Normal Phase in HPLC and UHPLC (USP L20)Diol packing material can be universally used in different polar modes (NP, RP and HILIC). Diol bonded phases are a versatile alternative to unbonded silica for normal phase separations with shorter equilibration times.The hydroxyl groups provide good selectivity without excessive retention, caused by the weaker H-bonding of the diol layer than of silanols. Some diol bonded phases have been developed specifically for applications in the HILIC mode.<h5>Properties</h5><ul><li>Separation mechanism: Hydrophilic interaction</li><li>Ultra pure, spherical high performance HPLC phase based on silica gel</li><li>Diol, no endcapping, with 5 % carbon content&nbsp;</li></ul><h5>Key features</h5><ul><li>High-class HPLC phase perfectly suited to take on routine analyses as well as the most ambitious chromatography tasks, classical Diol phase without endcapping and 5 % carbon content, outstanding mechanical and chemical stability.</li></ul><h5>Recommended application areas</h5><ul><li>Alternative to the silica packing with shorter equilibration time and comparable selectivity; due to the lower activity of these packings it can be also used for SEC-applications.</li></ul><img src="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/KNAUER_Diol_26fe64c2b9.webp" alt="KNAUER: Diol" srcset="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/thumbnail_KNAUER_Diol_26fe64c2b9.webp 156w," sizes="100vw" width="426" height="425"><blockquote>Tip: The most important column parameters for evaluation are retention time, peak symmetry and theoretical plates. Retention time to prove the reproducibility of measurements. Peak symmetry to estimate how good the column bed is packed (peak symmetry value of 1.0 is optimal). Theoretical plate numbers to determine the effectiveness of the HPLC column.</blockquote>Stationary phase Eurospher II 100 Diol is provided in these column types: analytical, semi-preparative and preparative.Eurospher II 100 Diol Preparative Standard Columns are available with these parameters:<ul><li>Column length (mm): 50, 150, 250</li><li>Column ID (mm): 20, 30, 50</li><li>Particle size (µm): 5, 10, 15</li></ul>Eurospher II 100 Diol Preparative dAX Columns with dynamic axial compression are available with these parameters:<ul><li>Column length (mm): 50, 150, 250</li><li>Column ID (mm): 25, 30, 50</li><li>Particle size (µm): 5, 10, 15</li></ul><h3>KNAUER Preparative HPLC Columns</h3>The right choice for all dimensions from semi-prep to batch chromatography to SMB.<ul><li>Modifications: Reversed Phase, HILIC, Normale Phase</li><li>Max. Pressure: 400–600 bar</li><li>Column Inner Diameter (ID): 16–50 mm in our shop, more on request</li><li>Column Brands: Eurospher, Eurospher II</li><li>Safe Investment: Robustness and durability based on superior technology</li><li>Application: Easy upscaling, as all materials are available from ultra high performance to preparative scale HPLC. You can also use our upscaling calculator.</li><li>Customizable: Standard flanged hardware &amp; dAX hardware with static or dynamic axial compression available</li></ul><img src="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/KNAUER_Preparative_HPLC_Columns_31bc2477c3.webp" alt="KNAUER: KNAUER Preparative HPLC Columns" srcset="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/thumbnail_KNAUER_Preparative_HPLC_Columns_31bc2477c3.webp 221w," sizes="100vw" width="1024" height="724"><h5>Preparative HPLC columns can be offered with two different hardware types:</h5><ul><li>Versatile standard flanged hardware for nearly any application task in batch chromatography</li><li>dAX Hardware with static and dynamic axial compression for an extended lifetime and multi-column chromatography like SMB processes</li></ul>

Products from category Diol HPLC columns - page 1

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Breathomics, Asthma & GC×GC: PH Stefanuto on Fighting the “Proof‑of‑Concept” Trap

Proton sharing in polycarboxylic acids in aqueous solution

Equip Your Laboratory for Autumn at a Better Price