Hongming Cai , Xinyu Wu , Shixin Jin , Yubin Liu , Xuyuan Liu , Kuaile Lin , Ning Ding
{"title":"Design, synthesis, and application of triazole-embedded maltose-neopentyl-glycol (TMNG) amphiphiles for membrane protein studies","authors":"Hongming Cai , Xinyu Wu , Shixin Jin , Yubin Liu , Xuyuan Liu , Kuaile Lin , Ning Ding","doi":"10.1016/j.carres.2025.109560","DOIUrl":"10.1016/j.carres.2025.109560","url":null,"abstract":"<div><div>Understanding membrane protein (MP) structure and function is less advanced than that of soluble proteins. Detergents are the primary reagents used in membrane protein studies, yet only a limited selection is employed in both fundamental and applied research. This study presents the design, synthesis, and application of novel triazole-embedded maltose-neopentyl-glycol (TMNG) amphiphiles for membrane protein studies. Utilizing Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), the synthesis integrates two maltose hydrophilic subunits with the two-tailed lipid component, overcoming scalability issues encountered in previous methods. Thermal stabilization evaluations show that some TMNGs have equal or improved stabilizing effects compared to the widely used detergent maltose–neopentyl glycol (LMNG).</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109560"},"PeriodicalIF":2.4,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144297882","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Unravelling the transglycosylation mechanism of Aspergillus oryzae β-galactosidase: The role of acceptor structure","authors":"Cecilia Porciuncula González , Carolina Fontana , Margot Paulino , Cecilia Giacomini , Gabriela Irazoqui","doi":"10.1016/j.carres.2025.109579","DOIUrl":"10.1016/j.carres.2025.109579","url":null,"abstract":"<div><div>β-Galactosidases catalyse the hydrolysis of β-<span>d</span>-galactosides and, in the presence of nucleophiles other than water, can perform transgalactosylation. This study explores the transgalactosylation activity of <em>Aspergillus oryzae</em> β-galactosidase, focusing on the impact of the acceptor structure. Lactic acid (LA) and its ethyl ester (EL) were evaluated as acceptors through the study of the kinetics of the reaction using thin-layer chromatography. The results showed that while lactic acid is not a viable acceptor, ethyl lactate generates a transgalactosylation product, identified by NMR spectroscopy as β-<span>d</span>-galactosyl-<span>l</span>-lactate ethyl ester. High concentrations of ethyl lactate reduced product hydrolysis, suggesting enzyme inhibition. Kinetic studies using <em>o</em>-Nitrophenyl β-<span>d</span>-galactopyranoside (ONPG) as a galactosyl donor substrate confirmed a substrate inhibition mechanism by ethyl lactate, with an inhibition constant (K<sub>i</sub>) of 625 ± 56 mM, comparable to other acceptors like ethylene glycol.</div><div>Molecular docking and dynamics simulations confirmed that esterifying the acceptor carboxyl group enhances transgalactosylation efficiency. <em>In silico</em> analyses confirmed key interactions between the enzyme and the acceptor, offering valuable insights into the molecular basis of transgalactosylation. These findings enhance our understanding of β-galactosidase selectivity and underscore its potential for synthesizing galactosides with applications in biocatalysis and biotechnology.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109579"},"PeriodicalIF":2.4,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144312697","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alexander Luttenberger , Elena Spari , André Culum , Tobias Dorn , Wilhelm Festl , Roland C. Fischer , Herwig Prasch , Franziska Schmutz , Arnold E. Stütz , Martin Thonhofer , Hansjörg Weber , Patrick Weber , Tanja M. Wrodnigg
{"title":"Stereoselective ring contractions in glycopyranosides as key-step en route to isoiminosugars","authors":"Alexander Luttenberger , Elena Spari , André Culum , Tobias Dorn , Wilhelm Festl , Roland C. Fischer , Herwig Prasch , Franziska Schmutz , Arnold E. Stütz , Martin Thonhofer , Hansjörg Weber , Patrick Weber , Tanja M. Wrodnigg","doi":"10.1016/j.carres.2025.109572","DOIUrl":"10.1016/j.carres.2025.109572","url":null,"abstract":"<div><div>Isoiminosugars are glycomimetics and selective and highly potent inhibitors for glycoside hydrolases. Their structural characteristics still remain a challenge and show the need for efficient synthetic approaches when compared to similar more easily available relatives. Herein, we provide a general synthetic concept for advanced derivatives of this compound class. A LiAlH<sub>4</sub> induced stereoselective 1,2-shift of C-4 to C-2 in O-2 tosylated <span>d</span>-glucopyranosides leading to ring-contracted C-2 branched <span>d</span>-ribofuranosides allows for convenient access to either C-2- or C-5a-elongated analogues of powerful β-galactosidase inhibitor 4-<em>epi</em>-isofagomine. Mechanistic insights into the synthetic key-step, as well as its broader application targeting <span>d</span>-gluco mimicking isoiminosugars are provided.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109572"},"PeriodicalIF":2.4,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144366800","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Step-wise and one-pot syntheses of the trisaccharide repeating unit of Proteus penneri 71 O-antigen","authors":"Tanmoy Halder, Sunil K. Yadav, Somnath Yadav","doi":"10.1016/j.carres.2025.109581","DOIUrl":"10.1016/j.carres.2025.109581","url":null,"abstract":"<div><div>Due to the importance of the capsular polysaccharides of bacterial pathogens from the perspective of eliciting human immune response and consequential developments of vaccines, they are important targets of synthetic efforts. Herein, we report the chemical synthesis of the trisaccharide repeating unit of the O-antigen capsular polysaccharide of <em>Proteus penneri</em> 71 by step-wise and one-pot approaches using suitably protected monosaccharide building blocks. A comparison of the yields of the products from the two strategies showed that the latter provided a higher yield (67%) than the former (56%).</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109581"},"PeriodicalIF":2.4,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144290508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Polysaccharides coated on mesoporous silica nanoparticles inhibit the inflammatory response for the treatment of sepsis","authors":"Sha Xiong , Yajie Jia , Xiaohui Liang","doi":"10.1016/j.carres.2025.109580","DOIUrl":"10.1016/j.carres.2025.109580","url":null,"abstract":"<div><div>To address the challenges of low antibiotic delivery efficiency and complex inflammatory microenvironments in sepsis therapy, we developed a multifunctional fluorescent nanoplatform, 1-PGA-2@MSN@Meropenem, for targeted drug delivery and hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>)-responsive detection. This system employs mesoporous silica nanoparticles (MSN) as carriers, coated with polygalacturonic acid (PGA) for enhanced stability, and functionalized with a fluorescent small molecule (Compound 1) and a natural antimicrobial agent (Compound 2). Comprehensive characterization confirmed its mesoporous structure (average pore size ∼3.4 nm), large surface area (216.4 m<sup>2</sup>/g), and successful drug loading and surface modification (FT-IR, PXRD). Fluorescence analysis revealed a strong emission at 670 nm under 390 nm excitation with a large Stokes shift (>270 nm), offering excellent signal-to-noise ratio and imaging potential. The probe exhibited a linear fluorescence response to H<sub>2</sub>O<sub>2</sub> over 0–40 μM (R<sup>2</sup> = 0.9893), with a high association constant (K<sub>a</sub> = 1.38 × 10<sup>5</sup> M<sup>−1</sup>) and outstanding selectivity. Furthermore, in an LPS-induced THP-1 macrophage inflammation model, the meropenem-loaded nanoparticles significantly downregulated pro-inflammatory cytokines TNF-α and IL-1β at the mRNA level, indicating their potential to mitigate sepsis-associated inflammation by suppressing macrophage-mediated immune responses. This work provides a promising strategy integrating drug delivery, biosensing, and immunomodulation for advanced sepsis management.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109580"},"PeriodicalIF":2.4,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144312696","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Sumit K. Singh , Anindra Sharma , Nidhi Mishra , Vinod K. Tiwari
{"title":"Growing impact of ‘Click chemistry’ inspired glycohybrid 1,2,3-Triazoles in organic synthesis","authors":"Sumit K. Singh , Anindra Sharma , Nidhi Mishra , Vinod K. Tiwari","doi":"10.1016/j.carres.2025.109571","DOIUrl":"10.1016/j.carres.2025.109571","url":null,"abstract":"<div><div>Carbohydrates, a most abundant natural product have fascinating structural features notably their high functional nature having multiple hydroxyl groups as well stereogenic centers which all together attracted the interest of synthetic chemists to explore them as valuable scaffolds in ligand design. In recent years, 1,2,3-triazole-linked sugar conjugates developed <em>via</em> regioselective CuAAC route have emerged as promising ligands in transition metal catalysis. These glycoconjugates have been applied in C–C and C–N bond-forming reactions, including Ullmann and Sonogashira couplings, particularly with Cu, Ni, and Pd catalysts. Their use has further extended to asymmetric catalysis, ligand-assisted activation, and sustainable synthesis. This review provides a concise overview of click-derived 1,2,3–triazole–sugar conjugates as promising ligands in transition metal catalysis, with highlighting their role in enhancing the catalytic reactivity, controlling the regio- and/or stereoselectivity, and improving the efficiency of metal-mediated transformations.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109571"},"PeriodicalIF":2.4,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144262938","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Charlotte Brusa , Murielle Muzard , Emelyne Jolly , Caroline Rémond , Richard Plantier-Royon
{"title":"Enzymatic synthesis of xylosides and xylobiosides featuring aromatic aglycones","authors":"Charlotte Brusa , Murielle Muzard , Emelyne Jolly , Caroline Rémond , Richard Plantier-Royon","doi":"10.1016/j.carres.2025.109573","DOIUrl":"10.1016/j.carres.2025.109573","url":null,"abstract":"<div><div>β-<span>d</span>-Xylopyranosides bearing a hydrophobic aglycon have been known for over fifty years as compounds that can enter cells and act as primers for the synthesis of glycosaminoglycan chains. A range of aromatic xylosides and xylobiosides were prepared by a xylanase-catalyzed transglycosylation reaction from commercially available beechwood xylans and aromatic alcohols. A comparison in the reactivity of aromatic primary alcohols and the corresponding aromatic alcohols with a phenol group showed better results for transglycosylation reactions with the latter. A comparison was also carried out for transglycosylation reactions with phenol and diphenol acceptors.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109573"},"PeriodicalIF":2.4,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144321866","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Structural characterization of the polysaccharide produced by Lactobacillus helveticus CNRZ32 and assignment of the function of genes involved in its biosynthesis","authors":"Marie-Rose Van Calsteren , Fleur Gagnon , Nancy Guertin , Christophe Gilbert","doi":"10.1016/j.carres.2025.109577","DOIUrl":"10.1016/j.carres.2025.109577","url":null,"abstract":"<div><div>Strain CNRZ32 of <em>Lactobacillus helveticus</em> was grown in chemically defined medium or milk, and its exopolysaccharide (EPS) was isolated from the supernatant or the whole culture and purified by TCA and acetone precipitations and solvent extractions. Purity was checked by gel permeation chromatography. The molecular mass determined by size-exclusion chromatography was 6.4 × 10<sup>5</sup> g/mol. Structural elucidation was performed by chemical, chromatographic, and spectroscopic methods. Monosaccharide and configuration analyses gave the following sugar composition: <span>d</span>-Gal, 2; <span>d</span>-Glc, 1; <span>d</span>-GlcNAc, 1; <span>l</span>-Rha, 3. Methylation analysis indicated the presence of terminal and 3,6-disubstituted Gal, 4-substituted Glc, 3,4,6-trisubstituted GlcNAc, as well as terminal and 2,4-disubstituted Rha. A phosphoethanolamine substituent was detected by NMR spectroscopy. On the basis of one- and two-dimensional homo- and heteronuclear NMR data, the structure of the EPS was consistent with a multibranched heptasaccharide repeating unit with the following sequence: {4[Rhaα-3]GlcNAc6<em>P</em>EtNβ-3[Galβ-6]Galα-4[Rhaα-2]Rhaβ-4Glcβ-}<sub><em>n</em></sub>. Electrospray MS and MS/MS data are given for oligosaccharides produced after deacetylation, deamination, and reduction. A correlation between the EPS sequence and genes of the <em>L. helveticus</em> CNRZ32 <em>eps</em> locus encoding putative enzymes responsible for the biosynthesis of the repeating unit is proposed. The structure is compared to that of EPSs produced by other <em>L. helveticus</em> strains.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109577"},"PeriodicalIF":2.4,"publicationDate":"2025-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144481786","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lingling Sun , Lifeng Zhu , Xiaoci Li , Weimin Jiang
{"title":"Drug-loaded composite materials based on polysaccharide carriers for alleviating myocardial cell damage","authors":"Lingling Sun , Lifeng Zhu , Xiaoci Li , Weimin Jiang","doi":"10.1016/j.carres.2025.109574","DOIUrl":"10.1016/j.carres.2025.109574","url":null,"abstract":"<div><div>Heart failure, a leading cause of mortality among cardiovascular disease patients, is primarily a consequence of chronic heart failure (CHF) and myocardial tissue damage associated with apoptosis. Leveraging the pharmacological success of Dapagliflozin, an SGLT-2 inhibitor known for reducing glucose reabsorption and its preventative efficacy against cardiovascular diseases, we have engineered and synthesized a novel derivative, compound 2, to enhance therapeutic outcomes. Furthermore, we utilized chitosan (CS) as a carrier matrix and integrated a bioactive compound, compound 1, synthesized from actinomycetes, to develop an antimicrobial drug delivery material, CS-1, designated for the administration of compound 2 (CS-1@2), which exhibits pH-responsive antimicrobial effects. The physicochemical properties, in vitro biological characteristics, and bioactivity of CS-1@2 were rigorously evaluated. Results indicated that CS-1 possesses a porous structure, facilitating accelerated release of compound 2 in mildly acidic conditions. In vitro cellular assays were conducted, establishing a CHF model using doxorubicin-induced AC16 cardiomyocytes. This study aims to elucidate the mechanisms through which CS-1@2 mitigates doxorubicin-induced damage in AC16 myocardial cells, highlighting its potential in CHF management. This study lays a promising foundation for targeted therapy of chronic heart failure (CHF) and promotes its translational application in personalized cardiovascular medicine.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109574"},"PeriodicalIF":2.4,"publicationDate":"2025-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144242360","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Total synthesis of the linker-armed tetrasaccharide repeating unit of the O-polysaccharide from E. coli O50","authors":"Subrata Das, Balaram Mukhopadhyay","doi":"10.1016/j.carres.2025.109563","DOIUrl":"10.1016/j.carres.2025.109563","url":null,"abstract":"<div><div>Synthesis of the tetrasaccharide repeating unit of the OPS from <em>E. coli</em> O50 is accomplished through rational protecting group manipulations on commercially available monosaccharides followed by stereoselective glycosylations. The target structure is achieved by [2 + 2]-block strategy and the challenging 1,2-<em>cis</em> or β-rhamnosidic linkage is formed using the hydrogen bond assisted aglycon delivery (HAD) technique. The final oligosaccharide in the form of its 2-aminoethyl glycoside is ready for conjugation with suitable aglycon towards the formation of bioactive glycoconjugate.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"555 ","pages":"Article 109563"},"PeriodicalIF":2.4,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144231105","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}