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Hydroxyl groups introducing NMR strategy for structural elucidation of a heptasaccharide isolated from Trillium tschonoskii. 羟基引入核磁共振技术对一种七糖进行结构解析。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 Epub Date: 2024-12-17 DOI: 10.1016/j.carres.2024.109359
Juan Song, Guangzhong Tu, Yue Liu, Si Liu, Yuting Zhang, Wenxi Yang, Xu Pang, Xiaojuan Chen, Haizhen Liang, Jie Zhang, Baiping Ma
{"title":"Hydroxyl groups introducing NMR strategy for structural elucidation of a heptasaccharide isolated from Trillium tschonoskii.","authors":"Juan Song, Guangzhong Tu, Yue Liu, Si Liu, Yuting Zhang, Wenxi Yang, Xu Pang, Xiaojuan Chen, Haizhen Liang, Jie Zhang, Baiping Ma","doi":"10.1016/j.carres.2024.109359","DOIUrl":"10.1016/j.carres.2024.109359","url":null,"abstract":"<p><p>A heptasaccharide was isolated from an active fraction of Trillium tschonoskii using HILIC and high-temperature PGC chromatography methods. UHPLC-Q/TOF-MS analysis gave this oligosaccharide a degree of polymerization (DP) of 7 and MS/MS showed that it has a six-carbon aldehyde glucan structure with the possible chain 1 → 4 connected. The structure was determined by series 1D and 2D NMR in two solvents D<sub>2</sub>O and DMSO‑d<sub>6</sub>. Using <sup>1</sup>H resonances of the -OH groups as the starting point and HSQC-TOCSY on the covalent structure definition for structural elucidation allowed this heptasaccharide to be uncovered. This heptasaccharide was elucidated as maltoheptaose via complete assignment of <sup>1</sup>H and <sup>13</sup>C with jigsaw H-C-OH pieces produced by HSQC-TOCSY at increasing mixing time. The significance of identifying maltoheptaose in Trillium tschonoskii indicates the high potential of -OH introducing strategy for other oligosaccharides' structural determination with relatively higher DP.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109359"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142876341","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 the conjugation ready tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi KR26. fontilapidosi Halomonas KR26 o -多糖偶联型四糖重复单元的合成。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 Epub Date: 2024-12-28 DOI: 10.1016/j.carres.2024.109371
Bijoy Rudra, Balaram Mukhopadhyay
{"title":"Synthesis of the conjugation ready tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi KR26.","authors":"Bijoy Rudra, Balaram Mukhopadhyay","doi":"10.1016/j.carres.2024.109371","DOIUrl":"10.1016/j.carres.2024.109371","url":null,"abstract":"<p><p>Synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi 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.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109371"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","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}
引用次数: 0
O-GlcNAc glycans in the mammalian extracellular environment. 哺乳动物细胞外环境中的O-GlcNAc聚糖。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 Epub Date: 2025-01-10 DOI: 10.1016/j.carres.2025.109378
Yohei Tsukamoto, Tetsuya Okajima
{"title":"O-GlcNAc glycans in the mammalian extracellular environment.","authors":"Yohei Tsukamoto, Tetsuya Okajima","doi":"10.1016/j.carres.2025.109378","DOIUrl":"10.1016/j.carres.2025.109378","url":null,"abstract":"<p><p>Extracellular O-GlcNAc is a unique post-translational modification that occurs in the epidermal growth factor-like (EGF) domain of the endoplasmic reticulum (ER) lumen. The EGF domain-specific O-GlcNAc transferase (EOGT), catalyzes the transfer of O-GlcNAc to serine/threonine residues of the C-terminal EGF domain. Thus, EOGT-dependent O-GlcNAc modifications are mainly found in selective proteins that are localized in the extracellular spaces or extracellular regions of membrane proteins. In mammals, O-GlcNAc glycans can be extended to oligosaccharide structures similar to other types of EGF domain-specific O-glycans. The in vivo importance of O-GlcNAc glycans in mammals has been demonstrated in a human congenital disease caused by EOGT mutations and is extensively supported by genetic deletion in mice. This article reviews the findings on the structure and biochemical mechanism of EOGT-catalyzed O-GlcNAc biosynthesis, modified proteins, and in vivo functions elucidated by recent research in mammals.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109378"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000670","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
Hydrophobic modification of starch via enzymatic grafting polymerization of fluorinated vinyl monomer. 含氟乙烯基单体酶接枝改性淀粉的研究。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 Epub Date: 2025-01-08 DOI: 10.1016/j.carres.2025.109376
Wenda Wang, Qiang Wang, Ping Wang
{"title":"Hydrophobic modification of starch via enzymatic grafting polymerization of fluorinated vinyl monomer.","authors":"Wenda Wang, Qiang Wang, Ping Wang","doi":"10.1016/j.carres.2025.109376","DOIUrl":"10.1016/j.carres.2025.109376","url":null,"abstract":"<p><p>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, <sup>19</sup>F 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.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109376"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","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}
引用次数: 0
Isolation and characterisation of a heparosan capsular polysaccharide and a core oligosaccharide from Moraxella lincolnii strain CCUG 52988. 林肯莫拉菌CCUG 52988中肝多糖荚膜多糖和核心寡糖的分离与鉴定。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 Epub Date: 2024-12-29 DOI: 10.1016/j.carres.2024.109361
Kosala S Ravikumaran, Samantha Armiento, Cristina De Castro, Antonio Molinaro, Jennifer C Wilson, Ian R Peak, I Darren Grice
{"title":"Isolation and characterisation of a heparosan capsular polysaccharide and a core oligosaccharide from Moraxella lincolnii strain CCUG 52988.","authors":"Kosala S Ravikumaran, Samantha Armiento, Cristina De Castro, Antonio Molinaro, Jennifer C Wilson, Ian R Peak, I Darren Grice","doi":"10.1016/j.carres.2024.109361","DOIUrl":"10.1016/j.carres.2024.109361","url":null,"abstract":"<p><p>Moraxella lincolnii 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-GlcpA-(1→4)-α-D-GlcpNAc-(1→]<sub>n</sub>, a glycosaminoglycan (GAG) also present in mammalian hosts. The core OS isolated was identified as a branched tetrasaccharide composed of: β-D-Glcp-(1→4)-[β-D-Glcp-(1→6)]-α-D-Glcp-(1→5)-α-Kdo-OH. This core OS structure is without heptose residues and is consistent with previously reported core OS structures from Moraxella 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 lgt3 were considered to form the LOS biosynthesis locus. This is the first report of the isolation of CPS and core OS from M. lincolnii.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109361"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","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":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Identification and structural characterization of glucosylceramides in Holothuria (Halodeima) grisea: Insights from TLC and NMR techniques. 水藻中糖基神经酰胺的鉴定和结构表征：来自TLC和NMR技术的见解。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 Epub Date: 2025-01-04 DOI: 10.1016/j.carres.2024.109374
Matheus Pires Miranda
{"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":"<p><p>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 Holothuria (Halodeima) grisea. 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.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109374"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","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}
引用次数: 0
Chemically modified chitosan as a functional biomaterial for drug delivery system. 化学修饰壳聚糖作为药物输送系统的功能性生物材料。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-01 Epub Date: 2024-12-06 DOI: 10.1016/j.carres.2024.109351
Devika Sajeev, Aparna Rajesh, R Nethish Kumaar, D Aswin, Rangasamy Jayakumar, Sreeja C Nair
{"title":"Chemically modified chitosan as a functional biomaterial for drug delivery system.","authors":"Devika Sajeev, Aparna Rajesh, R Nethish Kumaar, D Aswin, Rangasamy Jayakumar, Sreeja C Nair","doi":"10.1016/j.carres.2024.109351","DOIUrl":"10.1016/j.carres.2024.109351","url":null,"abstract":"<p><p>Chitosan is a natural polymer that can degrade in the environment and support green chemistry. It displays superior biocompatibility, easy access, and easy modification due to the reactive amino groups to transform or improve the physical and chemical properties. Chitosan can be chemically modified to enhance its properties, such as water solubility and biological activity. Modified chitosan is the most effective functional biomaterial that can be used to deliver the drugs to the targeted site. With diverse and versatile characteristics, it can be fabricated into various drug delivery systems such as membranes, beads, fibers, microparticles, composites, and scaffolds, for different drug delivery methods. Integrating nanotechnology with modified chitosan enhanced the delivery attributes of antibacterial, antifungal, antiviral, anticancer, anti-inflammatory, protein/peptides, and nucleic acids for intended use toward desired therapeutic outcomes. The review brings out an overview of the research regarding drug delivery systems utilizing modifying chitosan detailing the properties, functionality, and applications.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109351"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142821934","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 trends in the separation and analysis of chitooligomers. 壳寡聚物分离与分析的最新进展。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-01 Epub Date: 2024-11-28 DOI: 10.1016/j.carres.2024.109337
Lucie Petrásková, Pavla Bojarová
{"title":"Recent trends in the separation and analysis of chitooligomers.","authors":"Lucie Petrásková, Pavla Bojarová","doi":"10.1016/j.carres.2024.109337","DOIUrl":"10.1016/j.carres.2024.109337","url":null,"abstract":"<p><p>Chitosan is a widely used linear biopolymer composed mainly of glucosamine and to a lesser extent of N-acetylglucosamine units. Many biological activities of chitosan are attributed to its shorter oligomeric chains, which consist of chitosan prepared either by enzyme activity (lysozyme, bacterial chitinase) or chemically by acid-catalyzed hydrolysis (e.g. in the stomach). However, these processes always result in a mixture of shorter chitooligosaccharides with varying degrees of acetylation whereas for relevant results of biological studies it is necessary to work with a precisely defined material. In this review, we provide an overview and comparison of analytical methods leading to the determination of the degree of polymerization (DP), the degree of acetylation (DA), the fraction of acetylation (FA) and the acetylation patterns (PA) of chitooligosaccharide chains and of the current state of knowledge on chitooligosaccharide separation. This review aims to present the most promising routes to well-defined low molecular weight chitosan with low dispersity.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109337"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142790975","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
Transglycosylation behavior of Mucor hiemalis endo-β-N-acetylglucosaminidase to β-cyclodextrin derivatives with multivalent glucose moieties for synthesizing cyclodextrin-based oligosaccharide clusters. Mucor hiemalis endo-β-N-acetylglucosaminidase 对具有多价葡萄糖分子的 β-环糊精衍生物的转糖基化行为，用于合成基于环糊精的寡糖簇。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-01 Epub Date: 2024-12-10 DOI: 10.1016/j.carres.2024.109352
Yusuke Tomabechi, Yoshiki Oda, Kenji Yamamoto, Takashi Yamanoi
{"title":"Transglycosylation behavior of Mucor hiemalis endo-β-N-acetylglucosaminidase to β-cyclodextrin derivatives with multivalent glucose moieties for synthesizing cyclodextrin-based oligosaccharide clusters.","authors":"Yusuke Tomabechi, Yoshiki Oda, Kenji Yamamoto, Takashi Yamanoi","doi":"10.1016/j.carres.2024.109352","DOIUrl":"10.1016/j.carres.2024.109352","url":null,"abstract":"<p><p>We investigated the transglycosylation reaction of two types of oligosaccharide acceptors, i.e., β-cyclodextrin (CD) derivatives 1 and 2 conjugated with multiple glucose (Glc) units, catalyzed by endo-β-N-acetyl-glucosaminidase from Mucor hiemalis (Endo-M) using the oligosaccharide donor sialoglycopeptide (SGP). The acceptor specificity of the enzyme transglycosylation of 1 and 2 having seven Glc moieties within small nanoscale spatial regions on the β-CDs was investigated on the basis of the effect of the molar ratios of SGP to acceptors 1 or 2 with different spatial configurations on the transglycosylation behavior. The formation of the corresponding CD-based oligosaccharide clusters from Endo-M was also evaluated.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109352"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142869398","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 on the biological activities and the nutraceutical potential of chitooligosaccharides. 壳寡糖的生物活性及其营养潜力的研究进展。
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-01 Epub Date: 2024-11-28 DOI: 10.1016/j.carres.2024.109336
Makyson R S Leal, Luiza R A Lima, Natalie E R Rodrigues, Paulo A G Soares, Maria G Carneiro-da-Cunha, Priscilla B S Albuquerque
{"title":"A review on the biological activities and the nutraceutical potential of chitooligosaccharides.","authors":"Makyson R S Leal, Luiza R A Lima, Natalie E R Rodrigues, Paulo A G Soares, Maria G Carneiro-da-Cunha, Priscilla B S Albuquerque","doi":"10.1016/j.carres.2024.109336","DOIUrl":"10.1016/j.carres.2024.109336","url":null,"abstract":"<p><p>Chitooligosaccharides (CHOS) or chitosan oligosaccharides (COS) are oligomers mainly composed of d-glucosamine (GlcN) units and structured in a positively charged, basic, amino molecule obtained from the degradation of chitin/chitosan through physical, chemical, or enzymatic methods. CHOS display physicochemical properties attractive to applications from the food to the biomedical field, such as non-toxicity to humans, high water solubility, low viscosity, biocompatibility, and biodegradability. These properties also allow CHOS to exert important biological activities, for example, antioxidant, antimicrobial, anti-inflammatory, immunomodulatory, antitumor, and hypocholesterolemic ones, besides to exhibit applications in food systems, technological, and nutraceutical potential. Therefore, this study summarized the synthesis and chemical structure, biological functions, and mechanisms of action of CHOS; with this, we aimed to contribute to the knowledge about the application of CHOS from the food to the biomedical industries.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109336"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142784213","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
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