<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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<h4>Advanced PFAS Analytical Services</h4><h5>Ensuring Compliance, Safety and Environmental Responsibility</h5>Per- and polyfluoroalkyl substances (PFAS) are a group of synthetic chemicals widely used in industrial applications and consumer products. Their persistence in the environment and potential health risks have led to increasing regulatory scrutiny, particularly in drinking water and firefighting foam residues.<img src="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/ALS_Advanced_PFAS_Analytical_Services_c8d8b28b7c.jpg" alt="ALS: Advanced PFAS Analytical Services" srcset="https://storage.googleapis.com/labrulez-bucket-strapi-h3hsga3/thumbnail_ALS_Advanced_PFAS_Analytical_Services_c8d8b28b7c.jpg 245w," sizes="100vw" width="1604" height="502"><h4>Our Expertise</h4>We offer state-of-the-art analytical services for the detection and quantification of PFAS in:<ul><li>Drinking/ground/surface/waste water</li><li>Soil, sediment, sludge and biosolids</li><li>AFFF-contaminated sites and products</li></ul><h5>Using LC-MS/MS, our laboratories provide:</h5><ul><li>Ultra-trace level detection (ng range)</li><li>Analysis of over <a target="_blank" rel="noopener noreferrer" 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sizes="100vw" width="919" height="919"></blockquote><h4>Regulatory Context in Europe (2025)</h4>European legislation is rapidly evolving to address PFAS contamination:<ul><li><a target="_blank" rel="noopener noreferrer" href="https://eur-lex.europa.eu/legal-content/EN/LSU/?uri=oj:JOL_2020_435_R_0001">The EU Drinking Water Directive (2020/2184) </a>mandates monitoring of PFAS, with a parametric value of 0.10 μg/L for the sum of 20 PFAS compounds</li><li><a target="_blank" rel="noopener noreferrer" href="https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=OJ:L:2006:396:TOC">Reach Regulation 1907/2006</a> and the key <a target="_blank" rel="noopener noreferrer" href="https://eur-lex.europa.eu/eli/reg/2021/1297/oj/eng">Amendment Regulation 2021/1297</a>, targeting the C9-C14 perfluorocarboxylic acids and related substances</li><li><a target="_blank" rel="noopener noreferrer" href="https://www.consilium.europa.eu/en/press/press-releases/2025/04/10/soil-monitoring-law-council-reaches-deal-with-parliament/">The Soil Monitoring law</a> (provisional agreement april 2025) includes PFAS as part of the soil Health assessment</li><li><a target="_blank" rel="noopener noreferrer" href="https://environment.ec.europa.eu/topics/water/water-framework-directive_en">The Water Frame Directive </a>with EQS on surface and groundwater and considerations for sediments and biota</li></ul><h3>List of PFAS analytes and report limits for determining PFAS substances in water</h3>For the sum of PFAS, a limit of 0.1 μg/l has been set, which applies to 20 substances marked with an asterisk (*) in the text below.<h5>Group: Perfluoroalkyl carboxylic acids</h5>Analyte / Abbreviation / Standard method (μg/l) / Low-limit method (μg/l)<ul><li>Perfluorobutanoic acid / PFBA* / 0.01 / 0.002</li><li>Perfluoro-3-methoxypropanoic acid / PFMPA / 0.025 / 0.001</li><li>Perfluoropentanoic acid / PFPeA* / 0.01 / 0.0003</li><li>Perfluoro-4-methoxybutanoic acid / PFMBA / 0.025 / 0.001</li><li>Perfluorohexanoic acid / PFHxA* / 0.01 / 0.0003</li><li>Tetrafluoro-2-(heptafluoropropoxy) propanoic acid / HFPO-DA / 0.02 / 0.001</li><li>Perfluoroheptanoic acid / PFHpA* / 0.01 / 0.0003</li><li>4,8-dioxa-3H-perfluorononanoic acid / DONA / 0.01 / 0.002</li><li>7H-perfluoroheptanoic acid / HPFHpA / 0.01 / 0.001</li><li>Perfluorooctanoic acid / PFOA* / 0.005 / 0.0003</li><li>Perfluoro-3,7-dimethyloctanoic acid / P37DMOA / 0.01 / 0.001</li><li>Perfluorononanoic acid / PFNA* / 0.01 / 0.0003</li><li>Perfluorodecanoic acid / PFDA* / 0.01 / 0.0003</li><li>2H,2H,3H,3H-Perfluorooctanoic acid / H4PFUnDA / 0.02 / 0.0003</li><li>Perfluorooctanoic acid / PFUnDA* / 0.01 / 0.0003</li><li>Perfluorododecanoic acid / PFDoDA* / 0.01 / 0.0003</li><li>Perfluorotridecanoic acid / PFTrDA* / 0.01 / 0.0003</li><li>Perfluorotetradecanoic acid / PFTeDA / 0.025 / 0.0003</li><li>Perfluorohexadecanoic acid / PFHxDA / 0.05 / n.a.</li><li>Perfluorooctadecanoic acid / PFOcDA / 0.05 / n.a.</li></ul><h5>Group: Perfluoroalkylsulfonic acids</h5>Analyte / Abbreviation / Standard method (μg/l) / Low-limit method (μg/l)<ul><li>Perfluoropropanesulfonic acid / PFPrS / 0.02 / 0.001</li><li>Perfluoro(2-ethoxyethane)sulfonic acid / PFEESA / 0.1 / 0.001</li><li>Perfluorobutanesulfonic acid / PFBS* / 0.01 / 0.0003</li><li>Perfluoropentanesulfonic acid / PFPeS* / 0.01 / 0.0003</li><li>Perfluorohexanesulfonic acid / PFHxS* / 0.01 / 0.0003</li><li>Perfluoroheptanesulfonic acid / PFHpS* / 0.01 / 0.0003</li><li>Perfluorooctane sulfonic acid / PFOS* / 0.005 / 0.0003</li><li>n-Decafluoro-4-(pentafluoroethyl) cyclohexane sulfonic acid / PFECHS / 0.01 / 0.0003</li><li>Perfluorononane sulfonic acid / PFNS* / 0.01 / 0.0003</li><li>Perfluorodecane sulfonic acid / PFDS* / 0.01 / 0.0003</li><li>Perfluorooctadecane sulfonic acid / PFUnDS* / 0.01 / 0.001</li><li>Perfluorododecane sulfonic acid / PFDoDS* / 0.01 / 0.0003</li><li>Perfluorotridecane sulfonic acid / PFTrDS* / 0.02 / 0.001</li></ul><h5>Group: Fluorotelomeric sulfonates</h5>Analyte / Abbreviation / Standard method (μg/l) / Low-limit method (μg/l)<ul><li>4:2 fluorotelomeric sulfonate / 4:2 FTS / 0.01 / 0.0003</li><li>6:2 fluorotelomeric sulfonate / 6:2 FTS / 0.01 / 0.0003</li><li>8:2 fluorotelomeric sulfonate / 8:2 FTS / 0.01 / 0.0003</li><li>10:2 fluorotelomeric sulfonate / 10:2 FTS / 0.01 / n.a.</li></ul><h5>Group: Perfluorinated sulfonamides</h5>Analyte / Abbreviation / Standard method (μg/l) / Low-limit method (μg/l)<ul><li>N-methyl-perfluorooctanesulfonamide / MeFOSA / 0.05 / 0.002</li><li>N-ethyl perfluorooctane sulfonamide / EtFOSA / 0.05 / 0.002</li><li>N-methyl perfluorooctane sulfonamidoethanol / MeFOSE / 0.025 / 0.002</li><li>N-ethyl perfluorooctane sulfonamidoethanol / EtFOSE / 0.025 / 0.002</li></ul><h5>Group: Perfluorooctane sulfonamidoacetic acid derivatives</h5>Analyte / Abbreviation / Standard method (μg/l) / Low-limit method (μg/l)<ul><li>Perfluorooctane sulfonamidoacetic acid / FOSAA / 0.01 / 0.001</li><li>N-Methyl perfluorooctane sulfonamidoacetic acid / MeFOSAA / 0.01 / 0.001</li><li>N-Ethyl perfluorooctane sulfonamidoacetic acid / EtFOSAA / 0.01 / 0.001</li></ul><h5>Group: Fluorotelomeric carboxylic acids</h5>Analyte / Abbreviation / Standard method (μg/l) / Low-limit method (μg/l)<ul><li>3-Perfluoropropyl propanoic acid (3:3) / 3:3 FTCA / 0.1 / 0.0003</li><li>n-2-Perfluorohexyl ethanoic acid (6:2) / 6:2 FTCA / 0.1 / 0.001</li><li>3-Perfluoropentyl propanoic acid (5:3) / 5:3 FTCA / 0.02 / 0.001</li><li>2H-Perfluoro-2-octenoic acid (6:2) / 6:2 FTUCA / 0.02 / 0.001</li><li>3-Perfluoroheptyl propanoic acid (7:3) / 7:3 FTCA / 0.02 / 0.0003</li><li>n-2-Perfluorooctyl ethanoic acid (8:2) / 8:2 FTCA / 0.1 / 0.001</li><li>2H-Perfluoro-2-decanoic acid (8:2) / 8:2 FTUCA / 0.02 / 0.001</li></ul><h5>Group: Chlorinated perfluoroalkyl sulfonic acids</h5>Analyte / Abbreviation / Standard method 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