Carbohydrate Research最新文献

{"title":"Synthesis of trisaccharide antigens featuring colitose, abequose and fucose residues and assessment of antibody binding on antigen arrays","authors":"Nikita M. Podvalnyy ,&nbsp;Lisa Crone ,&nbsp;Daniela Paganini ,&nbsp;Michael B. Zimmermann ,&nbsp;Thierry Hennet","doi":"10.1016/j.carres.2024.109283","DOIUrl":"10.1016/j.carres.2024.109283","url":null,"abstract":"<div><div>Deoxy-hexose sugars, such as rhamnose and quinovose, and the dideoxy-hexoses colitose, abequose, and tyvelose are highly antigenic given that they are absent from animal glycoconjugates. To investigate the specificity of antibodies towards structurally similar carbohydrate epitopes found in bacteria, we synthesized trisaccharides containing colitose, abequose, and fucose motifs. Each trisaccharide was designed with a spacer ending with a primary amino group. These trisaccharide constructs were immobilized on O-succinimide coated glass slides alongside bacterial lipopolysaccharides (LPS) containing colitose, abequose, and fucose residues. We compared the recognition of the synthetic trisaccharides and natural LPS including structurally related epitopes by monoclonal and polyclonal antibodies targeting bacterial LPS. Additionally, we used arrays displaying the synthetic trisaccharides and natural LPS to assess the variability of IgA reactivity from breast milk samples towards the carbohydrate antigens. The results obtained underlined the cross-reactivity of polyclonal antibodies towards structurally related carbohydrate antigens and revealed a broad reactivity of breast milk-derived IgA towards the carbohydrate antigens tested. The significant cross-reactivity of antibodies towards structurally related LPS antigens may lead to false-positive detection of bacterial serotypes when used for diagnostic purposes.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109283"},"PeriodicalIF":2.4,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142342163","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":"High-yield production of completely linear dextrans and isomalto-oligosaccharides by a truncated dextransucrase from Ligilactobacillus animalis TMW 1.971","authors":"Oliver Müller,&nbsp;Daniel Wefers","doi":"10.1016/j.carres.2024.109284","DOIUrl":"10.1016/j.carres.2024.109284","url":null,"abstract":"<div><div>Several lactic acid bacteria are capable of producing water-soluble exopolysaccharides such as dextran from sucrose by using glucansucrases. Several recombinant glucansucrases were described, however, yields were often limited and most dextrans were branched at position <em>O</em>3. In this study, the dextransucrase from <em>Ligilactobacillus animalis</em> TMW 1.971 was recombinantly produced without its <em>N</em>-terminal variable region and used for dextran synthesis. The enzyme expressed well and showed very high total as well as transferase activities compared to other glucansucrases. It was able to transfer nearly all glucose from sucrose to oligo- and polymeric products under certain conditions (about 95 % of glucose transferred). The high efficiency of the enzyme made it possible to obtain absolute dextran yields of up to 214.9 g/L from a 1.5 M sucrose solution. Structural characterization of the products showed that the dextrans produced have a rather low molecular weight, a narrow size distribution, and are completely linear. Furthermore, we showed that various low molecular weight dextrans or 1,6-linked isomalto-oligosaccharides can be efficiently produced by acid hydrolysis. Overall, we demonstrated that <em>Ligilactobacillus animalis</em> TMW 1.971 dextransucrase can be used to efficiently synthesize dextrans with a quite unique structural composition. The dextrans produced have a high potential for further applications such as synthesis of copolymers or size standards with a very defined molecular structure.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109284"},"PeriodicalIF":2.4,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142364497","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":"Base-free trifluoroacetylation: From methyl glucopyranoside to cellulose nanofibers","authors":"Robert J. Nicholas,&nbsp;Nosa B. Idahagbon,&nbsp;Alexander Wei","doi":"10.1016/j.carres.2024.109282","DOIUrl":"10.1016/j.carres.2024.109282","url":null,"abstract":"<div><div>Trifluoroacetic anhydride (TFAA) reacts smoothly with low molecular weight carbohydrates and cellulose nanofibers (CNFs) under base-free conditions. Methyl α- and β-<span>d</span>-glucopyranoside were used as model compounds to optimize reaction conditions, which were then applied to lyophilized CNFs for surface modification. ATR-IR spectroscopy and powder X-ray diffraction were employed to characterize the modified CNFs. Trifluoroacetylation for 4 h yields a degree of substitution (DS) of 0.4 acyl groups per anhydroglucose unit while maintaining a crystallinity index near 50 %. DS values were quantified by gravimetry, acid–base titration after saponification, and a novel approach utilizing solution ¹⁹F NMR spectroscopy which offers greater accuracy than the other techniques. This study presents an efficient, base-free method for derivatizing carbohydrates as well as surface functionalization of CNFs with trifluoroacetyl groups, potentially expanding their application in fiber-reinforced thermoplastic composites.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109282"},"PeriodicalIF":2.4,"publicationDate":"2024-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142324103","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 and pharmacological evaluation of nature-inspired phenacyl glycosides","authors":"Emmanilo Delar ,&nbsp;Yanis Tigherghar ,&nbsp;Laurie Girard ,&nbsp;Mohamed Haddad ,&nbsp;Charles Ramassamy ,&nbsp;Jean Legault ,&nbsp;Charles Gauthier","doi":"10.1016/j.carres.2024.109281","DOIUrl":"10.1016/j.carres.2024.109281","url":null,"abstract":"<div><div>Phenylethanoid glycosides are a well-studied class of bioactive compounds found throughout the plant kingdom. In contrast, research on the synthesis and pharmacological activity of phenacyl glycosides, a specific subgroup of phenylethanoid glycosides with a ketone functionality at the alpha position of the phenol ring, has been limited. In this study, we report the synthesis, cytotoxic, antiviral, and anti-inflammatory evaluation of a series of 18 4′-hydroxyphenacyl glycosides. These compounds consist of six different sugar residues (<em>β</em>-<span>d</span>-glucose, <em>β</em>-<span>d</span>-galactose, <em>α</em>-<span>l</span>-arabinose, <em>β</em>-<span>d</span>-xylose, <em>α</em>-<span>l</span>-rhamnose, and <em>β</em>-<span>d</span>-glucuronic acid) and display three distinct methoxylation patterns at the phenacyl ring, similar to the substitution motifs of anthocyanins. We obtained the target phenacyl glycosides in high yield and stereoselectivity through the coupling of benzoyl-protected trichloroacetimidate glycosyl donors and corresponding acetophenones. Our work represents the first total synthesis of the natural products 4′-hydroxyphenacyl-<em>β</em>-<span>d</span>-glucopyranoside (<strong>1</strong>) and 4′-hydroxy-3′-methoxyphenacyl-<em>β</em>-<span>d</span>-glucopyranoside (<strong>2</strong>). None of the phenacyl glycosides showed cytotoxicity against the tested cell lines. Notably, several of the synthesized compounds exhibited antiviral activity, with natural product <strong>2</strong> being the most active against herpes simplex virus type 1, while phenacyl arabinoside <strong>9</strong> and natural product <strong>2</strong> were the most active against human coronavirus OC43. Natural product <strong>2</strong> significantly inhibited the production of interleukin-6 in lipopolysaccharide-stimulated microglia cells. Overall, our findings highlight the importance of the sugar residue and phenacyl ring substitution pattern in modulating the antiviral activity of phenacyl glycosides. Natural product <strong>2</strong> and phenacyl arabinoside <strong>9</strong> emerge as promising leads for the development of antiviral agents.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109281"},"PeriodicalIF":2.4,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142356698","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 2,3-diazido-2,3-dideoxy-β-d-mannosides and 2,3-diazido-2,3-dideoxy-β-d-mannuronic acid via stereoselective anomeric O-alkylation","authors":"Rama Banjara,&nbsp;Prakash Thapa,&nbsp;Shailja Hitesh Kela,&nbsp;Fenglang Wu,&nbsp;Jianglong Zhu","doi":"10.1016/j.carres.2024.109279","DOIUrl":"10.1016/j.carres.2024.109279","url":null,"abstract":"<div><div>Stereoselective synthesis of 2,3-diazido-2,3-dideoxy-β-<span>d</span>-mannosides has been accomplished via Cs₂CO₃-mediated anomeric <em>O</em>-alkylation of 2,3-diazido-2,3-dideoxy-β-<span>d</span>-mannoses with primary electrophiles. Selective oxidation of the C6 primary alcohol of the 2,3-diazido-2,3-dideoxy-β-<span>d</span>-mannoside successfully produced corresponding 2,3-diazido-2,3-dideoxy-β-<span>d</span>-mannuronic acid.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109279"},"PeriodicalIF":2.4,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142320210","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":"Efficient synthesis for each of the eight stereoisomers of the iminosugars lentiginosine and 1,4-dideoxy-1,4-imino-D-arabinitol (DAB)","authors":"Louis J. Liotta,&nbsp;Jessica Antoine,&nbsp;Leighanne A. Brammer Basta,&nbsp;Andrew S. Campbell,&nbsp;Gabrielle Y. Cole,&nbsp;Kristen A. Demick Brazile,&nbsp;Natalie M. Dogal Gardner,&nbsp;Megan E. Fitzgerald,&nbsp;Jean E.K. Francois,&nbsp;Brian M. French,&nbsp;Sara L. Garafola,&nbsp;Catherine A. Giannetti,&nbsp;Eve A. Granatosky,&nbsp;Alycen M. Harney,&nbsp;James T. Hummel,&nbsp;Andrew P. Joyce,&nbsp;Mitchell H. Keylor,&nbsp;Jasmine A. Khubchandani,&nbsp;Claudia Korzeniecki,&nbsp;Diana C. Lieberman,&nbsp;Kerstin L. Tougas","doi":"10.1016/j.carres.2024.109280","DOIUrl":"10.1016/j.carres.2024.109280","url":null,"abstract":"<div><div>Herein, we describe the efficient, diastereoselective syntheses of the iminosugars 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) <strong>1b</strong>, lentiginosine <strong>3a</strong>, and the seven stereoisomers of each of these iminosugars starting from 4-benzoyl-6-deoxy-6-iodoglycopyranosides <strong>47</strong> with yields ranging from 38 % to 68 % for the DAB and isomers <strong>1a-1h</strong> and from 44 % to 89 % for the lentiginosine and isomers <strong>3a-3h</strong>. We also report the syntheses of the eight stereoisomers of the 4-benzoyl-6-deoxy-6-iodoglycopyranosides <strong>47</strong> from commercially available sugars. Key to the iminosugar syntheses is a single multistep reaction that converts the 4-benzoyl-6-deoxy-6-iodoglycopyranosides <strong>47</strong> to a vinyl pyrrolidine through a one-pot zinc mediated reductive elimination, followed by a reductive amination and finally an intramolecular nucleophilic substitution. Strategic selection of the amine utilized in the reductive amination and the functionalization of the intermediate carbon-carbon double bond provides access to a vast array of iminosugars.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109280"},"PeriodicalIF":2.4,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142320209","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":"Purification and characterization of α-fucosidase from Dichostereum sordulentum 1488","authors":"Lorena Herrera ,&nbsp;María Eugenia Cedrés ,&nbsp;Paula Rodríguez Bonnecarrere ,&nbsp;Cecilia Giacomini","doi":"10.1016/j.carres.2024.109278","DOIUrl":"10.1016/j.carres.2024.109278","url":null,"abstract":"<div><div>Biological glycans mediate several physiological processes, thus altered glycosylation patterns can lead to different diseases such as autoimmune, infectious, chronic anti-inflammatory diseases, or even cancer. In fact, alterations in fucosylation in either N- or <em>O</em>-glycans are among the most frequent changes in glycosylation patterns associated with cancer. Therefore, elucidation of the role of glycoconjugate glycans is essential for understanding the development of pathologies where they are involved. In this sense glycosidases are excellent tools, since they catalyse the selective removal of sugar residues, allowing the evaluation of changes in their biological role due to glycan removal. This work describes the purification and characterization of a α-fucosidase from the fungus <em>Dichostereum sordulentum</em> 1488. It is a homodimer with a molecular weight of 214 kDa and optimum pH and temperature of 4.0 and 70 °C respectively. It has a K_M of 0.27 mM and V_Max of 3.3 μmoles PNP/min per mg for the substrate <em>p</em>-nitrophenyl-α-<span>l</span>-fucopyranoside, showing a substrate inhibition profile. It showed high specificity for the hydrolysis of fucose linked by α-(1,2) bonds. The identification, purification, and characterization of this new α-fucosidase is highly relevant for enlarging the availability of glycosidases for use as tools for glycan elucidation.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109278"},"PeriodicalIF":2.4,"publicationDate":"2024-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142307089","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":"The K129 capsular polysaccharide produced by Acinetobacter baumannii MAR 15–4076 has the same composition as K84 but differs in the linkage between units altering the overall branching topology","authors":"Nikolay P. Arbatsky ,&nbsp;Alexander S. Shashkov ,&nbsp;Mikhail M. Shneider ,&nbsp;Yulia V. Mikhailova ,&nbsp;Andrey A. Shelenkov ,&nbsp;Eugene A. Sheck ,&nbsp;Anastasia A. Kasimova ,&nbsp;Nadezhda A. Kalinchuk ,&nbsp;Johanna J. Kenyon ,&nbsp;Yuriy A. Knirel","doi":"10.1016/j.carres.2024.109273","DOIUrl":"10.1016/j.carres.2024.109273","url":null,"abstract":"<div><div>Capsular polysaccharide (CPS) is a heteroglycan that coats the cell surface of most isolates of the important Gram-negative bacterial pathogen, <em>Acinetobacter baumannii.</em> Strain MAR 15–4076, a clinical isolate recovered in Russia in 2015, was found to carry the KL129 sequence at the CPS biosynthesis K locus. The CPS was isolated from the strain and studied by sugar analysis, Smith degradation, one- and two-dimensional ¹H and ¹³C NMR spectroscopy. It was composed of branched pentasaccharide units that include a →3)-α-<span>l</span>-Rha<em>p</em>-(1 → 3)-α-<span>l</span>-Rha<em>p</em>-(1 → 3)-β-<span>d</span>-Glc<em>p</em>NAc-(1→ mainchain and α-<span>d</span>-Man<em>p</em>NAc-(1 → 3)-<span>l</span>-Rha<em>p</em> side branch. Though the pentasaccharide units are identical to those that make up the K84 CPS produced by <em>A. baumannii</em> LUH5540, the units are linked differently via the substitution of an alternate <span>l</span>-Rha<em>p</em> residue, resulting in a difference in the overall topology of the CPS. This was due to the replacement of the Wzy polymerase gene encoded at the K locus.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109273"},"PeriodicalIF":2.4,"publicationDate":"2024-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142320208","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":"Interaction between reacetylated chitosan and albumin in alcalescent media","authors":"Inesa V. Blagodatskikh ,&nbsp;Oxana V. Vyshivannaya ,&nbsp;Nikita A. Tishchenko ,&nbsp;Evgeniya A. Bezrodnykh ,&nbsp;Vladimir E. Piskarev ,&nbsp;Rinat R. Aysin ,&nbsp;Yurij A. Antonov ,&nbsp;Victor N. Orlov ,&nbsp;Vladimir E. Tikhonov","doi":"10.1016/j.carres.2024.109277","DOIUrl":"10.1016/j.carres.2024.109277","url":null,"abstract":"<div><p>Interaction of chitosan and its derivatives with proteins of animal blood at blood pH relevant conditions is of a particular interest for construction of antimicrobial chitosan/protein-based drug delivery systems. In this work, the interaction of a series of <em>N</em>-reacetylated oligochitosans (RA-CHI) having <em>M</em>_<em>w</em> of 10–12 kDa and differing in the degree of acetylation (DA 19, 24, and 40 %) with bovine serum albumin (BSA) in alkalescent media is described in first. It is shown that RA-CHI forms soluble complexes with BSA in solutions with pH 7.4 and a low ionic strength. Light scattering study shows that soluble RA-CHI complexes have spherical form with the radius of about 100 nm. Circular dichroism, fluorescent spectroscopy, and micro-IR spectroscopy studies show that the secondary structure of BSA in soluble complexes remain intact. Isothermal titration calorimetry of RA-CHI with DA 24 % and BSA mixing in the buffers with different ionization heats reveals a significant contribution of electrostatic forces to the binding process and an additional ionization of chitosan due to the proton transfer from the buffer substance. An increase of ionic strength to the blood relevant value 0.15 M suppresses the binding. It is shown that application of RA-CHI with higher DA value leads to a decrease in the affinity of RA-CHI to BSA and an alteration of the interaction mechanism. The finding opens an opportunity to the application of N-reacetylated chitosan derivatives in the complex systems compatible with blood plasma proteins.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109277"},"PeriodicalIF":2.4,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243850","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":"Regioselective sulfation of alginate at 2-O-position of mannuronic acid unit with Py∙SO3 in DMSO","authors":"Karl Martin Ingerma ,&nbsp;Indrek Reile ,&nbsp;Rando Tuvikene","doi":"10.1016/j.carres.2024.109276","DOIUrl":"10.1016/j.carres.2024.109276","url":null,"abstract":"<div><p>Alginates are brown algal polysaccharides consisting of β-D-mannuronic (M) and α-<span>l</span>-guluronic acid (G) residues linked with 1→4 glycosidic bonds. To functionalize these natural resources for biomedical use, alginates can be chemically modified, including by sulfation. Here regioselective sulfation of alginates at M-2 in DMSO with Py∙SO₃ is described, by either sulfating alginates directly or through using alginates with added protecting groups (PG-s), including TBDMS-ether, Piv-, Bz-esters and intramolecular 3,6-lactone. Highest regioselectivity was found by sulfating TBDMS- and Piv-protected alginates, with over 65 % of M-residues being 2-<em>O</em>-sulfated. However significant reduction in molecular weight was found when alginates were sulfated in DMSO. Results from this work will allow a degree of control over substitution patterns in sulfated alginates. This will allow to more accurately determine structure-property relationships in biomedical research.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109276"},"PeriodicalIF":2.4,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142243848","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}