Carbohydrate Research最新文献_第4页

Antigenicity evaluation of the synthetic trisaccharides related to Plesiomonas shigelloides serotype O51 O-antigen containing an acetamidino group. 含乙酰氨基基的志贺单胞菌O51 o型抗原相关合成三糖的抗原性评价。

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-16 DOI: 10.1016/j.carres.2025.109388

Chunjun Qin, Wei Han, Guangzong Tian, Xiaopeng Zou, Anna Maciejewska, Jolanta Lukasiewicz, Peter H Seeberger, Jing Hu, Jian Yin

{"title":"Antigenicity evaluation of the synthetic trisaccharides related to Plesiomonas shigelloides serotype O51 O-antigen containing an acetamidino group.","authors":"Chunjun Qin, Wei Han, Guangzong Tian, Xiaopeng Zou, Anna Maciejewska, Jolanta Lukasiewicz, Peter H Seeberger, Jing Hu, Jian Yin","doi":"10.1016/j.carres.2025.109388","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109388","url":null,"abstract":"Bacterial surface polysaccharides are widely decorated with diverse rare functional groups. An understanding of the role of these functional groups in immunological activity of the glycans is required for the development of carbohydrate-based treatment against bacterial infectious diseases. Here, the antigenicity evaluation of synthetic trisaccharide 1 related to Plesiomonas shigelloides serotype O51 lipopolysaccharide (LPS) O-antigen and its acetamido derivative 2 was achieved to elucidate the immunological importance of O-antigen structure. The rabbit antisera with high titers of IgG and IgM were collected after immunization with purified P. shigelloides serotype O51 LPS. Glycan microarray screening results showed that both IgG and IgM in rabbit antisera bound specifically to trisaccharides 1 and 2, indicating that the trisaccharide repeating unit is a key antigenic epitope of P. shigelloides serotype O51 O-antigen, while the acetamidino group has no influence on the antigenicity. This finding provides key information for glycoconjugate vaccine design for P. shigelloides serotype O51.","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109388"},"PeriodicalIF":2.4,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000674","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}

引用次数: 0

Synthesis of 2-hydroxy analogues of castanospermine, 1-epi-castanospermine and their iminooctitols from sugar-derived lactam. 糖源内酰胺合成2-羟基castanospermine、1-epi-castanospermine及其亚氨基糖醇。

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-14 DOI: 10.1016/j.carres.2025.109385

Nagaraja Ingaladal, Ravi S Lankalapalli

引用次数: 0

Unraveling the diversity of protein-carbohydrate interfaces: Insights from a multi-scale study. 揭示蛋白质-碳水化合物界面的多样性：来自多尺度研究的见解。

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-13 DOI: 10.1016/j.carres.2025.109377

Aria Gheeraert, Frédéric Guyon, Serge Pérez, Tatiana Galochkina

{"title":"Unraveling the diversity of protein-carbohydrate interfaces: Insights from a multi-scale study.","authors":"Aria Gheeraert, Frédéric Guyon, Serge Pérez, Tatiana Galochkina","doi":"10.1016/j.carres.2025.109377","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109377","url":null,"abstract":"Protein-carbohydrate interactions play a crucial role in numerous fundamental biological processes. Thus, description and comparison of the carbohydrate binding site (CBS) architecture is of great importance for understanding of the underlying biological mechanisms. However, traditional approaches for carbohydrate-binding protein analysis and annotation rely primarily on the sequence-based methods applied to specific protein classes. The recently released DIONYSUS database aims to fill this gap by providing tools for CBS comparison at different levels: both in terms of protein properties and classification, as well as in terms of atomistic CBS organization. In the current study, we explore DIONYSUS content using a combination of the suggested approaches in order to evaluate the diversity of the currently resolved non-covalent protein-carbohydrate interfaces at different scales. Notably, our analysis reveals evolutionary convergence of CBS in proteins with distinct folds and coming from organisms across different kingdoms of life. Furthermore, we demonstrate that a CBS structure based approach has the potential to facilitate functional annotation for the proteins with missing information in the existing databases. In particular, it provides reliable information for numerous carbohydrate-binding proteins from rapidly evolving organisms, whose analysis is particularly challenging for classical sequence-based methods.","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109377"},"PeriodicalIF":2.4,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000690","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}

引用次数: 0

A review of the latest advancements in using β-cyclodextrin-based as supramolecular catalysts for Heck reactions. 综述了以β-环糊精为基础的Heck反应超分子催化剂的最新研究进展。

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-13 DOI: 10.1016/j.carres.2025.109381

Sara Payamifar, Majid Abdouss, Shahrzad Javanshir, Ahmad Poursattar Marjani

{"title":"A review of the latest advancements in using β-cyclodextrin-based as supramolecular catalysts for Heck reactions.","authors":"Sara Payamifar, Majid Abdouss, Shahrzad Javanshir, Ahmad Poursattar Marjani","doi":"10.1016/j.carres.2025.109381","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109381","url":null,"abstract":"The Heck reaction is one of the most well-known C-C (carbon-carbon) coupling reactions and was identified with the Nobel Prize in Chemistry in 2010. These reactions have been broadly utilized to prepare a different spectrum of heterocycles with applications in agrochemical and pharmaceutical industries. These reactions are commonly catalyzed by palladium due to its tolerance and expansive variousness of functional groups, which bears a remarkable power in creating C-C bonds. Carbohydrate chemistry is a significant and crucial part of the organic chemistry field. Among existing carbohydrates, β-cyclodextrins (β-CDs) are natural cyclic oligosaccharides that contain glucose monomers and have played an active role in nearly every industrial and scientific field, attention and interest in them never aged. CDs can be utilized as a beneficial catalyst in numerous aqueous organic conversions. Their derivatives have demonstrated remarkable activity in water-mediated organic synthesis and are currently of continuing interest to multiple scientists in different fields. Being non-toxic, accessible, biodegradable, readily functionalized, low-cost, renewable, and producible in large-scale amounts are several of the benefits of CDs that make them a suitable nominee for catalyst applications. Different β-CDs catalysts have recently been widely employed for various C-C bond coupling reactions like the Heck coupling. Here, we review the latest advancements in using CD-based catalysts for Heck reactions.","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109381"},"PeriodicalIF":2.4,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000672","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}

引用次数: 0

Injectable vancomycin loaded hyaluronic acid-chitosan hydrogel for the treatment of Staphylococcus aureus septic arthritis. 万古霉素负载透明质酸-壳聚糖水凝胶注射治疗金黄色葡萄球菌脓毒性关节炎。

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-13 DOI: 10.1016/j.carres.2025.109384

K Kumaran, Anil Kumar Vasudevan, R Jayakumar, Raja Biswas

{"title":"Injectable vancomycin loaded hyaluronic acid-chitosan hydrogel for the treatment of Staphylococcus aureus septic arthritis.","authors":"K Kumaran, Anil Kumar Vasudevan, R Jayakumar, Raja Biswas","doi":"10.1016/j.carres.2025.109384","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109384","url":null,"abstract":"Staphylococcus aureus (S. aureus) is a Gram positive opportunistic pathogen and a major cause for bacterial septic arthritis. Vancomycin is the preferred antibiotic for the treatment of methicillin resistance S. aureus septic arthritis. Patients undergoing vancomycin treatment need to be hospitalized and their serum vancomycin level should be monitored, as increase in vancomycin concentration in serum may lead to hepatotoxicity. To overcome vancomycin mediated cytotoxicity, we have prepared a local injectable delivery system by incorporating vancomycin into hyaluronic acid (HA)-chitosan (van-HA-chitosan) hydrogel. The prepared van-HA-chitosan hydrogel was characterized using Fourier Transform Infrared Spectroscopy (FTIR) and rheometer. The van-HA-chitosan hydrogel is injectable, has shear thinning behaviour; and is hemo- and cyto-compatible. In vitro drug release assay showed that 95 % of vancomycin was released from the hydrogel in 8 days. Under in vitro conditions the load of S. aureus decreased from 6.4 Log10 CFU/ml to 3.5 Log10 CFU/ml when treated with van-HA-chitosan hydrogel for 6 h. Significant decrease in bacterial counts was observed when S. aureus infected synovial fluid and bone samples were treated with van-HA-chitosan hydrogel. Our results suggest that the prepared van-HA-chitosan could be used for the treatment of septic arthritis caused by S. aureus.","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109384"},"PeriodicalIF":2.4,"publicationDate":"2025-01-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000677","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}

引用次数: 0

Structural elucidation of the O-antigen polysaccharide from shigatoxin-producing E. coli O179 using genetic information, NMR spectroscopy and the CASPER program.

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-10 DOI: 10.1016/j.carres.2025.109382

Carolina Fontana, Andrej Weintraub, Göran Widmalm

{"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, Andrej Weintraub, Göran Widmalm","doi":"10.1016/j.carres.2025.109382","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109382","url":null,"abstract":"The serological properties of the O-antigen polysaccharide region of the lipopolysaccharides are used to differentiate E. coli strains into serogroups. In this study, we report the structure elucidation of the O-specific chain of E. coli O179 using NMR data, the program CASPER and analysis of biosynthetic information available in the E. coli 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-d-Manp-(1→4)-β-d-Manp-(1→3)-d-GlcpNAc 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-d-GlcpA-(1→3)-[β-d-Glcp-(1→2)]β-d-Manp-(1→4)-β-d-Manp-(1→3)-β-d-GlcpNAc-(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 E. coli O6 and O188, S. boydii type 16, and the capsular polysaccharide of E. coli K43, explaining the serological cross-reactivities observed with strains belonging these O- and K-antigen groups.","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"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":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of a di-O-acylated deoxynojirimycin (DNJ) derivative and evaluation of its antibacterial and antibiofilm activity against Staphylococcus aureus and Stenotrophomonas maltophilia.

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2025-01-10 DOI: 10.1016/j.carres.2025.109379

Anna Esposito, Daniele D'Alonzo, Maria Stabile, Vincenzo Firpo, Antonella Migliaccio, Rosaria Artiano, Stefano D'Errico, Eliana De Gregorio, Annalisa Guaragna

{"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, Daniele D'Alonzo, Maria Stabile, Vincenzo Firpo, Antonella Migliaccio, Rosaria Artiano, Stefano D'Errico, Eliana De Gregorio, Annalisa Guaragna","doi":"10.1016/j.carres.2025.109379","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109379","url":null,"abstract":"Herein we report the synthesis of a novel di-O-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-O-lauroyl DNJ derivative enhanced the antibacterial effect of gentamicin and amikacin against S. aureus and S. maltophilia 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 S. aureus, it was able to significantly reduce the viability of S. aureus and S. maltophilia 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 12.","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"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":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Recent advances in chemical synthesis of phosphodiester linkages found in fungal mannans 真菌甘露聚糖中磷酸二酯链化学合成的最新进展

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2024-11-22 DOI: 10.1016/j.carres.2024.109325

Zuchao Ma , Harry E. Ensley , Douglas W. Lowman , Michael D. Kruppa , David L. Williams

{"title":"Recent advances in chemical synthesis of phosphodiester linkages found in fungal mannans","authors":"Zuchao Ma , Harry E. Ensley , Douglas W. Lowman , Michael D. Kruppa , David L. Williams","doi":"10.1016/j.carres.2024.109325","DOIUrl":"10.1016/j.carres.2024.109325","url":null,"abstract":"<div><div>Fungal mannans are located on the exterior of the fungal cell wall, where they interact with the environment and, ultimately, the human host. Mannans play a major role in shaping the innate immune response to fungal pathogens. Understanding the phosphodiester linkage and mannosyl repeat units in the acid-labile portion of mannans is crucial for comprehending their structure/activity relationships and for development of anti-fungal vaccines and immunomodulators. The phosphodiester linkages connect the acid-stable and acid-labile portions of the mannan polymer. Phosphate groups are attached to positions 4 and/or 6 of mannosyl repeat units in the acid-stable portion and to position 1 of mannosyl repeat units in the acid-labile portion. This review focuses on the synthesis of phosphodiester linkages as an approach to the development of mannan glycomimetics, which are based on natural product fungal mannans. Development of successful synthetic strategies for the phosphodiester linkages may enable the production of mannan glycomimetics that elicit anti-fungal immune responses against existing and emerging fungal pathogens, such as Candida albicans and Candida auris.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109325"},"PeriodicalIF":2.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142722419","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}

引用次数: 0

Chemical extension and glycodendrimer formation of the matriglycan decasaccharide, -(3Xylα1-3GlcAβ1)5- and its affinity for laminin matriglycan 十糖-(3Xylα1-3GlcAβ1)5-的化学延伸和糖二聚体形成及其与层粘连蛋白的亲和力

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2024-11-22 DOI: 10.1016/j.carres.2024.109328

Kota Kotera , Ren Miyamoto , Gakuto Mochizuki , Takahiro Tamura , Noriyoshi Manabe , Yoshiki Yamaguchi , Jun-ichi Tamura

{"title":"Chemical extension and glycodendrimer formation of the matriglycan decasaccharide, -(3Xylα1-3GlcAβ1)5- and its affinity for laminin","authors":"Kota Kotera , Ren Miyamoto , Gakuto Mochizuki , Takahiro Tamura , Noriyoshi Manabe , Yoshiki Yamaguchi , Jun-ichi Tamura","doi":"10.1016/j.carres.2024.109328","DOIUrl":"10.1016/j.carres.2024.109328","url":null,"abstract":"<div><div>Muscle tissue is stabilized by the strong interaction between laminin and matriglycan. Matriglycan is a polysaccharide composed of the repeating disaccharide, -3Xylα1-3GlcAβ1-, and is a pivotal part of the core M3 O-mannosyl glycan. Patients with muscular dystrophy cannot synthesize matriglycan or the core M3 O-mannosyl glycan due to a defect in or the lack of glycosyltransferases owing to glycan synthesis. Therefore, a supply of matriglycan may be a powerful tool for reconstructing muscle tissue in these patients. We herein report the synthesis of a matriglycan-repeating decasaccharide and a dendrimer comprising three branches of the decasaccharide. The glycan was regio- and stereoselectively synthesized by the stepwise addition of the corresponding disaccharide unit. The immobilized decasaccharide and glycodendrimer bound to laminin-G-like domains 4 and 5 of laminin-α2. The dissociation constants of the decasaccharide and dendrimer obtained from bio-layer interferometry were estimated to be 4.4 × 10−8 M and 6.8 × 10−8 M, respectively, showing higher affinity than those of a matriglycan-repeating hexasaccharide (1.6 × 10−7 M) and the dendrimer (1.8 × 10−7 M).</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109328"},"PeriodicalIF":2.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702510","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}

引用次数: 0

Synthesis of a heptasaccharide N-glycan comprising two mannose-6-phosphate residues 合成包含两个 6-磷酸甘露糖残基的七糖 N-聚糖

IF 2.4 3区化学

Carbohydrate Research Pub Date : 2024-11-20 DOI: 10.1016/j.carres.2024.109327

Nozomi Ishii , Andrea Mascherpa , Antony J. Fairbanks

引用次数: 0