Carbohydrate Research最新文献

{"title":"Structural elucidation of the O-antigen polysaccharide from shigatoxin-producing E. coli O179 using genetic information, NMR spectroscopy and the CASPER program","authors":"Carolina Fontana ,&nbsp;Andrej Weintraub ,&nbsp;Göran Widmalm","doi":"10.1016/j.carres.2025.109382","DOIUrl":"10.1016/j.carres.2025.109382","url":null,"abstract":"<div><div>The serological properties of the O-antigen polysaccharide region of the lipopolysaccharides are used to differentiate <em>E. coli</em> strains into serogroups. In this study, we report the structure elucidation of the O-specific chain of <em>E. coli</em> O179 using NMR data, the program CASPER and analysis of biosynthetic information available in the <em>E. coli</em> O-antigen Database (ECODAB). The presence of genes that encode enzymes involved in the biosynthesis of the GDP-Man and UDP-GlcA within the O-antigen gene cluster of the bacteria indicates that the corresponding residues could be present in the polysaccharide. Furthermore, the occurrence of four genes that encode for glycosyltransferases indicates that the polysaccharide is composed of pentasaccharide repeating units; a bioinformatics approach based on predictive glycosyltransferase functions present in ECODAB revealed that the β-<span>d</span>-Man<em>p</em>-(1→4)-β-<span>d</span>-Man<em>p</em>-(1→3)-<span>d</span>-Glc<em>p</em>NAc structural element could be present in the O-specific chain. NMR spectroscopy data obtained from homonuclear and heteronuclear 2D NMR spectra (¹H,¹H-TOCSY, ¹H,¹³C-HSQC, ¹H,¹³C-H2BC and ¹H,¹³C-HMBC) were analyzed using the CASPER program, revealing the following arrangement of monosaccharide residues as the most probable structure: →4)-α-<span>d</span>-Glc<em>p</em>A-(1→3)-[β-<span>d</span>-Glc<em>p</em>-(1→2)]β-<span>d</span>-Man<em>p</em>-(1→4)-β-<span>d</span>-Man<em>p</em>-(1→3)-β-<span>d</span>-Glc<em>p</em>NAc-(1→, which was further confirmed using 2D homonuclear ¹H,¹H-COSY and ¹H,¹H-NOESY spectra. The functions of the α-gluconosyltransferase and the β-glucosyltransferase were predicted using structural alignment of AlphaFold-predicted 3D structures. This O-antigen polysaccharide shares structural similarities with those of <em>E. coli</em> O6 and O188, <em>S. boydii</em> type 16, and the capsular polysaccharide of <em>E. coli</em> K43, explaining the serological cross-reactivities observed with strains belonging these O- and K-antigen groups.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109382"},"PeriodicalIF":2.4,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027850","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of a di-O-acylated deoxynojirimycin (DNJ) derivative and evaluation of its antibacterial and antibiofilm activity against Staphylococcus aureus and Stenotrophomonas maltophilia","authors":"Anna Esposito ,&nbsp;Daniele D'Alonzo ,&nbsp;Maria Stabile ,&nbsp;Vincenzo Firpo ,&nbsp;Antonella Migliaccio ,&nbsp;Rosaria Artiano ,&nbsp;Stefano D'Errico ,&nbsp;Eliana De Gregorio ,&nbsp;Annalisa Guaragna","doi":"10.1016/j.carres.2025.109379","DOIUrl":"10.1016/j.carres.2025.109379","url":null,"abstract":"<div><div>Herein we report the synthesis of a novel di-<em>O</em>-acylated DNJ derivative, conceived to study whether iminosugar derivatization with a lipophilic acyl moiety could positively affect its antibacterial properties. The well-known PS-TPP/I₂/ImH activating system was used to readily install the acyl chains on the iminosugar, leading to the desired compound in high yield. Biological assays revealed that a di<em>-O</em>-lauroyl DNJ derivative enhanced the antibacterial effect of gentamicin and amikacin against <em>S. aureus</em> and <em>S. maltophilia</em> strains, respectively, suggesting a potential role as antibiotic adjuvant. Furthermore, even though this compound displayed only a weak concentration-dependent inhibitory effect on biofilm formation in <em>S. aureus</em>, it was able to significantly reduce the viability of <em>S. aureus</em> and <em>S. maltophilia</em> preformed biofilms. The results confirm the antibacterial potential of piperidine iminosugars and open the way to further studies involving novel lipophilic derivatives to optimize the antibacterial adjuvant effect herein observed for iminosugar <strong>12</strong>.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109379"},"PeriodicalIF":2.4,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143037024","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Hydrophobic modification of starch via enzymatic grafting polymerization of fluorinated vinyl monomer","authors":"Wenda Wang,&nbsp;Qiang Wang,&nbsp;Ping Wang","doi":"10.1016/j.carres.2025.109376","DOIUrl":"10.1016/j.carres.2025.109376","url":null,"abstract":"<div><div>The synthesis of starch grafted with poly (hexafluorobutyl methacrylate) (PHFBMA) was achieved using the horseradish peroxidase (HRP)/acetophenone (ACAC) green initiating system. The modified starch was characterized through FT-IR, ¹⁹F NMR, XPS and EDS to confirm the successful grafting of PHFBMA onto starch backbone. The SEM analysis revealed that the introduction of PHFBMA led to a partial disruption of the crystalline structure of starch, suggesting that PHFBMA did not undergo physical adsorption onto starch. Compared to natural starch film, the modified starch film displays a significantly enhanced hydrophobicity, which can lead to substantial improvements in both the hydrophobicity and tensile properties when applied to hydrophilic paper substrates.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109376"},"PeriodicalIF":2.4,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142969739","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":"Identification and structural characterization of glucosylceramides in Holothuria (Halodeima) grisea: Insights from TLC and NMR techniques","authors":"Matheus Pires Miranda","doi":"10.1016/j.carres.2024.109374","DOIUrl":"10.1016/j.carres.2024.109374","url":null,"abstract":"<div><div>Sea cucumbers are widely used in oriental cuisine due to their medicinal properties. Antioxidant, antifungal, antiviral, anticancer and neuroprotective activities have already been identified in several species and in different tissues. Among the class of compounds with biological activity are cerebrosides, which have important functions for the proper functioning of cells, especially neuronal cells. The identification of this class of compounds can be carried out using simple techniques such as thin layer chromatography (TLC) or more sophisticated techniques such as nuclear magnetic resonance (NMR), providing different information depending on the technique used. Therefore, this work aimed to identify the presence of cerebrosides in different tissues of <em>Holothuria (Halodeima) grisea</em>. TLC analysis and separation on a silica column made it possible to accurately identify the positive fractions for cerebrosides. This selectivity is crucial to ensure that the compounds identified are genuine cerebrosides, eliminating interference from other non-pertinent bands. NMR spectroscopy analyses confirmed the presence of glucosylceramide in the tissues studied. The identification of a β-glucose linked to the ceramide, with specific structural characteristics such as hydroxyl on the 3′ carbon of the sphingosine and a double bond between the 4′ and 5′ carbons, highlights the accuracy of the structural determination obtained with the techniques used.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109374"},"PeriodicalIF":2.4,"publicationDate":"2025-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000668","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":"Structure characterization and preliminary immune activity of a glucomannan purified from Allii Tuberosi Semen","authors":"Huiwen Li ,&nbsp;Aigen Fu ,&nbsp;Heping Hui ,&nbsp;Feng Jia ,&nbsp;Huan Wang ,&nbsp;Tong Zhao ,&nbsp;Jing Wei ,&nbsp;Peijuan Zhang ,&nbsp;Wuying Lang ,&nbsp;Kejuan Li ,&nbsp;Xuansheng Hu","doi":"10.1016/j.carres.2025.109375","DOIUrl":"10.1016/j.carres.2025.109375","url":null,"abstract":"<div><div>A novel glucomannan, named ATSW-1, was obtained from <em>Allii Tuberosi Semen</em> by ion and gel permeation chromatography purification. Its structure was characterized using high-performance chromatography, Fourier transform infrared spectroscopy, gas chromatography-mass spectrometry, and nuclear magnetic resonance spectroscopy. The <em>in vitro</em> immune activities of ATSW-1 were examined using the Cell Counting Kit-8, the neutral red phagocytosis assay, and the secretion of related cytokines. The results showed that the molecular weight of ATSW-1 was 35.9 kDa and mainly constituted of mannose, glucose, and arabinose with a molar ratio of 1:0.72:0.04. Its main backbone was composed of →4)-β-D-Glc<em>p</em>-(1→, →4)-β-D-Man<em>p</em>-(1→, and →4,6)-α-D-Man<em>p</em>-(1→, with the branches β-D-Glc<em>p</em>-(1→, α-L-Ara<em>f</em>-(1→ and →5)-α-L-Ara<em>f</em>-(1→ linkage substituted at C-6 position of →4)-α-D-Man<em>p</em>-(1 → . ATSW-1 significantly enhanced immune responses, increasing the phagocytic activity of RAW264.7 cells by 1.52 times compared to the blank control group. Further investigations revealed that ATSW-1 promotes immune activity by upregulating the NO, TNF-α, and IL-6 secretion. These findings provide a foundation for the potential development and application of <em>Allii Tuberosi Semen</em> polysaccharides in functional foods or immune-related therapeutics.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109375"},"PeriodicalIF":2.4,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143022377","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cancer cell adhesion property on all-chitin composite films with reduced crystallinity","authors":"Masayasu Totani,&nbsp;Hiroyuki Shinchi,&nbsp;Jun-ichi Kadokawa","doi":"10.1016/j.carres.2024.109373","DOIUrl":"10.1016/j.carres.2024.109373","url":null,"abstract":"<div><div>We previously prepared self-reinforced chitin composite (SR-ChC) films, also called all-chitin composites, comprising two components, that is, scale-down chitin nanofibers (SD-ChNFs) with high crystallinity and scale-down low-crystalline chitin (SD-LC-Ch) matrixes. In this study, we precisely evaluated hydrophilicity under water enviromental conditions and its effect on cell adhesion using human-derived cancer cells on the SR-ChC film surfaces. The surface analysis of the SR-ChC films with reduced crystallinity revealed reorientation of the molecular chain assemblies with amino groups in the SD-LC-Ch components in water. Consequently, the amount of the SD-LC-Ch components gave rise to increasing the number of hydrophilic amino groups on the film surfaces, which resulted in efficiency of cell adhesion and elongation. This study concludes that the hydrophilic SD-LC-Ch components in the lower crystalline SR-ChC films strongly contribute to exhibiting new functions, related to interaction with biological substrates, such as cells.</div><div>© 2017 ElsevierInc.Allrightsreserved.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109373"},"PeriodicalIF":2.4,"publicationDate":"2024-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142929964","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Isolation and characterisation of a heparosan capsular polysaccharide and a core oligosaccharide from Moraxella lincolnii strain CCUG 52988","authors":"Kosala S. Ravikumaran ,&nbsp;Samantha Armiento ,&nbsp;Cristina De Castro ,&nbsp;Antonio Molinaro ,&nbsp;Jennifer C. Wilson ,&nbsp;Ian R. Peak ,&nbsp;I. Darren Grice","doi":"10.1016/j.carres.2024.109361","DOIUrl":"10.1016/j.carres.2024.109361","url":null,"abstract":"<div><div><em>Moraxella lincolnii</em> is a Gram-negative bacterium that resides in the upper respiratory tract (URT) of humans and may have a role as a member of a protective microbial community. Structural characterisation studies of its outer membrane glycan structures are very limited. We report here the isolation and structural characterisation (NMR, GLC-MS) of a capsular polysaccharide (CPS) and an oligosaccharide (OS) (lipooligosaccharide (LOS)-derived) isolated from strain CCUG 52988. The repeat disaccharide unit of the isolated CPS is unmodified heparosan: [→4)-β-D-Glc<em>p</em>A-(1→4)-α-D-Glc<em>p</em>NAc-(1→]_n, a glycosaminoglycan (GAG) also present in mammalian hosts. The core OS isolated was identified as a branched tetrasaccharide composed of:</div><div>β-D-Glc<em>p</em>-(1→4)-[β-D-Glc<em>p</em>-(1→6)]-α-D-Glc<em>p</em>-(1→5)-α-Kdo-OH.</div><div>This core OS structure is without heptose residues and is consistent with previously reported core OS structures from <em>Moraxella</em> spp. Genes encoding homologues of the Lgt6 and Lgt3 glycosyltransferases that catalyse these additions were identified in the genome. Additional glycosyltransferases and other proteins encoded downstream of <em>lgt3</em> were considered to form the LOS biosynthesis locus. This is the first report of the isolation of CPS and core OS from <em>M. lincolnii</em>.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109361"},"PeriodicalIF":2.4,"publicationDate":"2024-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142945028","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Block synthesis of Forssman pentasaccharide GalNAcα1-3GalNAcβ1-3Galα1-4Galβ1-4Glcβ in the form of 3-aminopropyl glycoside","authors":"Inna S. Popova ,&nbsp;Marina A. Sablina ,&nbsp;Ivan M. Ryzhov ,&nbsp;Darya O. Anisimova ,&nbsp;Tatiana V. Ovchinnikova ,&nbsp;Tatiana V. Tyrtysh ,&nbsp;Elena Yu. Korchagina ,&nbsp;Alexander O. Chizhov ,&nbsp;Alexander S. Paramonov ,&nbsp;Nicolai V. Bovin","doi":"10.1016/j.carres.2024.109370","DOIUrl":"10.1016/j.carres.2024.109370","url":null,"abstract":"<div><div>A total chemical synthesis of spacer-armed Forssman pentasaccharide is reported. The choice of the 2(donor) + 3(acceptor) block scheme, the optimal combination of a limited number of simple protecting groups and the sequence of deprotection steps allowed to achieve the high yield and stereoselectivity of glycosylation and to avoid losses during deprotection. The target pentasaccharide was obtained in a 10-mg scale. ¹H and ¹³C NMR spectra of the Forssman pentasaccharide were completely assigned with the use of various 2D-NMR experiments.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109370"},"PeriodicalIF":2.4,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142963764","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":"Selection of alkaliphilic Bacillus pectate lyases based on reactivity and pH-dependent stability in simulated environment for industrial applications","authors":"S.G. Sree Agash,&nbsp;R. Rajasekaran","doi":"10.1016/j.carres.2024.109372","DOIUrl":"10.1016/j.carres.2024.109372","url":null,"abstract":"<div><div>Pectate lyases, known for their alkaliphilic nature, are ideal for industrial applications that require specific pH conditions, particularly in industries such as textiles and pulp extraction. These enzymes, primarily from the polysaccharide lyase family 1 (PL1) of different microbial sources, play a vital role in polysaccharide degradation. Given the potent pectinolytic activity of <em>Bacillus</em> pectate lyases, targeting these enzymes is crucial for identifying the most effective candidates. To address challenges in enzyme selection, we examined the initial catalytic interactions of <em>Bacillus</em> species N16-5 (sp_N16-5), <em>Bacillus</em> species TS-47 (sp_TS-47), and <em>Bacillus</em> species subtilis strain 168 (sub_168) with pectin using molecular docking, focusing on the binding of pectin to the active-site tunnel region. We employed steered molecular dynamics simulations to analyze the disassociation period of pectin, where sp_N16-5 demonstrated higher compactness and we applied a semi-empirical quantum mechanical approach for reaction modeling. Our analysis through NPT ensemble-based dynamics analysis emphasised the structural stability and compactness required to withstand high-production conditions. We identified <em>Bacillus</em> species N16-5 (sp_N16-5) as the most efficient pectinolytic lyase, as it showed strong affinity, reactivity and higher interaction, also sp_N16-5 shows its enthalpy of reaction at 9 kcal/mol with a lower activation energy barrier at 27 kcal/mol which is closest to the typical range among the chosen <em>Bacillus</em> pectate lyase, enabling rapid pectin conversion alongside low energy input. Outcomes from the pH-dependent molecular dynamics revealed the sp_N16-5 to possess a greater structural endurability, comparatively, this study streamlines the screening process for selecting optimal <em>Bacillus</em> pectate lyases through <em>in-silico</em> investigation for industrial applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109372"},"PeriodicalIF":2.4,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142913705","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":"Synthesis of the conjugation ready tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi KR26","authors":"Bijoy Rudra,&nbsp;Balaram Mukhopadhyay","doi":"10.1016/j.carres.2024.109371","DOIUrl":"10.1016/j.carres.2024.109371","url":null,"abstract":"<div><div>Synthesis of the tetrasaccharide repeating unit of the <em>O</em>-polysaccharide from <em>Halomonas fontilapidosi</em> KR26 was accomplished through a convergent [2 + 2]-block strategy using rationally protected monosaccharide synthons derived from commercially available sugars. The target tetrasaccharide was synthesized in the form of its 2-azidoethyl glycoside to ensure further conjugation with specific aglycons without hampering the reducing end stereochemistry. Use of only acyl/aryl protecting groups was targeted to keep the terminal azido-group intact for the utilization of “Click chemistry” for further conjugations.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"Article 109371"},"PeriodicalIF":2.4,"publicationDate":"2024-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142913707","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}