Carbohydrate Research最新文献

{"title":"Carboxyl-converting titration versus other methods for the uronic acid content analysis of alginate oligosaccharide","authors":"Meng Shao ,&nbsp;Yue Yang ,&nbsp;Hao Liu ,&nbsp;Hui Zhou ,&nbsp;Yuanyuan Sun ,&nbsp;Xia Zhao ,&nbsp;Guangli Yu ,&nbsp;Youjing Lv ,&nbsp;Quancai Li","doi":"10.1016/j.carres.2025.109424","DOIUrl":"10.1016/j.carres.2025.109424","url":null,"abstract":"<div><div>This study presents a carboxyl-conversing titration method for determining the uronic acid content of alginate oligosaccharide (AOS). All C6 carboxyl groups on the monosaccharide residues of AOS were initially converted into carboxylates, which were subsequently transformed into carbonates through carbonization and incineration. Quantification was finally done through acid titration. The AOS content, which was represented by the amount of monosaccharide residues (ManA and GulA residues) in AOS sample, was calculated based on the stoichiometric relationship between the C6 carboxyl group and monosaccharide residue. To evaluate its performance, the carboxyl-conversing titration method was compared with the sulfuric acid-carbazole method and 1-phenyl-3-methyl-5-pyrazolone (PMP) pre-column derivatization high performance liquid chromatography (PMP-HPLC) method. The content of the uronic acid in AOS sample were detected 96.24 % ± 0.42 % using the carboxyl-conversing titration method, 186.85 ± 0.49 % (ManA/GulA = 1/1 as the reference standard) using the sulfuric acid-carbazole method, and 3.00 ± 0.08 % using the PMP-HPLC method. The carboxyl-conversing titration method demonstrated the highest accuracy of the content value. The validation of this method was also confirmed in the terms of specificity, limits of detection and quantification, recovery, repeatability, intermediate precision and durability. Compared to the sulfuric acid-carbazole and PMP-HPLC methods, the carboxyl-conversing titration method was proved easy to operate, reliable, and independent of reference standards. This innovative method offers a promising solution for accurately determining AOS content in laboratory and industrial settings.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109424"},"PeriodicalIF":2.4,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143403567","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":"Recent development on stereoselective intramolecular O-glycosylation methodology","authors":"Anindra Sharma ,&nbsp;Manoj K. Jaiswal ,&nbsp;Mangal S. Yadav ,&nbsp;Danish Ansari ,&nbsp;Rama P. Tripathi ,&nbsp;Vinod K. Tiwari","doi":"10.1016/j.carres.2025.109415","DOIUrl":"10.1016/j.carres.2025.109415","url":null,"abstract":"<div><div>Carbohydrates are increasingly recognized for their versatility as scaffolds in biological, pharmaceutical and biotechnological applications, due to their structural diversity, biocompatibility, hydrophilicity, low toxicity, bioavailability, and excellent ADME properties. The important role of carbohydrates in biological systems deepens, the demand for well-defined and anomerically pure carbohydrates in biomedical research has surged. Chemical synthesis remains the most viable method to meet this demand, despite the inherent challenges in glycosylation reactions. Carbohydrate oligomers, in particular, pose significant difficulties due to the need for complex protecting and leaving group modifications, functionalization, labour-intensive purification, and detailed characterization. A precise stereo and regio-control during glycosylation remains one of the major challenges in organic synthesis. To enhance the selectivity in glycosylation products, the concept of 'Intramolecular Glycosylation' was developed, offering a more advanced and efficient alternative route to conventional methods. Various intramolecular glycosylation methods can be classified primarily into three categories: Intramolecular Aglycone Delivery (IAD), Leaving Group-based Intramolecular Glycosylation, and the Molecular Clamp concept. This review article explores the fundamentals of these three methodologies, their significant advancements, and highlights their growing impact on the stereoselective synthesis of numerous bioactive <em>O</em>-glycosides, glycans with diverse functionalities, complex oligosaccharides, and various macrocycles with definite stereoselectivity.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109415"},"PeriodicalIF":2.4,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143526633","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":"“Biological evaluation of 3D-Printed chitosan-based scaffolds for tissue engineering”","authors":"Zahra Behrooznia,&nbsp;Jhamak Nourmohammadi,&nbsp;Zahra Mohammadi,&nbsp;Fatemeh Shabani,&nbsp;Rahele Mashhadi","doi":"10.1016/j.carres.2025.109416","DOIUrl":"10.1016/j.carres.2025.109416","url":null,"abstract":"<div><div>Chitosan is a natural polysaccharide with excellent biocompatibility, biodegradability, and antibacterial capabilities, making it a good candidate for tissue engineering. 3D printing has revolutionized biomaterial fabrication owing to its precision, customization, and ability to create complex structures. This article aims to provide an overview of the current advances in 3D printing techniques for fabricating scaffolds based on chitosan and its derivatives. It also describes various printing methods, including extrusion bioprinting technique, inkjet bioprinting, stereolithography, digital light processing, and indirect 3D printing for controlling porosity, mechanical strength, and biological characteristics of chitosan scaffolds for a variety of tissues, like bone, vascular, cardiac, cartilage, and skin. This review also examines the biological properties of 3D-printed chitosan scaffolds. The advancements in biological performance and 3D printing technology indicate a promising future for developing flexible, customized scaffolds consisting of chitosan.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109416"},"PeriodicalIF":2.4,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143437023","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":"Phosphorylated chitosan from the internal bone of Sepia kobiensis (Hoyle, 1885) and their inhibition against oral pathogens","authors":"Preetha Srinivasan ,&nbsp;Annathai Pitchai ,&nbsp;Pasiyappazham Ramasamy","doi":"10.1016/j.carres.2025.109413","DOIUrl":"10.1016/j.carres.2025.109413","url":null,"abstract":"<div><div>Phosphorylated chitosan, derived from the internal bone of <em>Sepia kobiensis</em> (Hoyle, 1885), has been investigated for its antimicrobial properties against oral pathogens. Chitosan's solubility in water and its biological effectiveness were enhanced through the alteration of its composition with orthophosphoric acid and dimethylformamide (DMF). Structural analysis for both chitosan and phosphorylated chitosan was performed using FTIR spectroscopy, field emission scanning electron microscopy (FESEM), and X-ray diffraction (XRD). The antimicrobial efficacy of chitosan and phosphorylated chitosan was assessed against clinically isolated human pathogens, including <em>Streptococcus mutans</em>, <em>Escherichia coli</em>, <em>Pseudomonas aeruginosa</em>, and <em>Candida tropicalis</em>. The highest inhibition zone, with a diameter of 23 ± 1.33 mm, was observed against <em>P. aeruginosa</em> for chitosan, while phosphorylated chitosan recorded a 25 ± 2.05 mm inhibition zone against <em>E. coli</em>. The findings of this study indicate that phosphorylated chitosan, with its potent antimicrobial properties, could serve as a possible antimicrobial drug for oral pathogens, sourced from a natural and sustainable origin.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109413"},"PeriodicalIF":2.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143205410","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":"pH-responsive paclitaxel prodrug encapsulated in a polypeptide-chitosan polymer delivery system for osteosarcoma treatment","authors":"Yunfei Lin,&nbsp;Bing Wang","doi":"10.1016/j.carres.2025.109414","DOIUrl":"10.1016/j.carres.2025.109414","url":null,"abstract":"<div><div>Osteosarcoma, a highly invasive and metastatic primary bone malignancy, remains a significant clinical challenge due to the limited improvement in overall survival despite advances in treatment strategies. This highlights the urgent need for the development of more effective therapeutic options. In response, we have developed a novel paclitaxel (PTX)-loaded nanodrug system, <strong>PLGA-CS-1@PTX</strong>, by incorporating a synthesized epoxy-tetrapeptide derivative (<strong>compound 1</strong>) with poly(lactic-co-glycolic acid) (PLGA) and chitosan (CS), forming the <strong>PLGA-CS-1 composite system</strong>. The system was thoroughly characterized for its physicochemical properties, including morphology, particle size, and in vitro release behavior. Scanning electron microscopy (SEM) confirmed the nanostructure of the particles, with <strong>particle sizes around 170 nm</strong> and a <strong>narrow PDI (&lt;0.15)</strong>, indicating a uniform distribution. In vitro release studies showed a <strong>pH-responsive release profile</strong>, with <strong>84.8 %</strong> of PTX released at pH <strong>5.4</strong> after <strong>65 h</strong> of incubation, compared to <strong>68.1 %</strong> at pH <strong>6.4</strong> and <strong>14.8 %</strong> at pH <strong>7.4</strong>, demonstrating good <strong>drug release control</strong> in acidic environments. Biological assays demonstrated significant inhibition of osteosarcoma cell proliferation in both <strong>HOS</strong> and <strong>U2OS</strong> cell lines, with a <strong>dose-dependent reduction</strong> in <strong>SPICE1</strong> expression, suggesting that <strong>PLGA-CS-1@PTX</strong> can effectively suppress the proliferative activity of osteosarcoma cells by modulating SPICE1 levels. The hydrophobic segment of the peptide enhanced the drug loading capacity and minimized side effects, improving the overall safety profile of the system. This composite system effectively integrates the strengths of each component, offering a promising, safe, and efficient strategy for osteosarcoma treatment with great potential for clinical application.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109414"},"PeriodicalIF":2.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143373045","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":"Recent trends in the separation and analysis of chitooligomers","authors":"Lucie Petrásková,&nbsp;Pavla Bojarová","doi":"10.1016/j.carres.2024.109337","DOIUrl":"10.1016/j.carres.2024.109337","url":null,"abstract":"<div><div>Chitosan is a widely used linear biopolymer composed mainly of glucosamine and to a lesser extent of <em>N</em>-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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 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}

{"title":"Chemically modified chitosan as a functional biomaterial for drug delivery system","authors":"Devika Sajeev ,&nbsp;Aparna Rajesh ,&nbsp;R. Nethish Kumaar ,&nbsp;D. Aswin ,&nbsp;Rangasamy Jayakumar ,&nbsp;Sreeja C. Nair","doi":"10.1016/j.carres.2024.109351","DOIUrl":"10.1016/j.carres.2024.109351","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 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}

{"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 ,&nbsp;Yoshiki Oda ,&nbsp;Kenji Yamamoto ,&nbsp;Takashi Yamanoi","doi":"10.1016/j.carres.2024.109352","DOIUrl":"10.1016/j.carres.2024.109352","url":null,"abstract":"<div><div>We investigated the transglycosylation reaction of two types of oligosaccharide acceptors, i.e., β-cyclodextrin (CD) derivatives <strong>1</strong> and <strong>2</strong> conjugated with multiple glucose (Glc) units, catalyzed by endo-β-<em>N</em>-acetyl-glucosaminidase from <em>Mucor hiemalis</em> (Endo-M) using the oligosaccharide donor sialoglycopeptide (SGP). The acceptor specificity of the enzyme transglycosylation of <strong>1</strong> and <strong>2</strong> 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 <strong>1</strong> or <strong>2</strong> with different spatial configurations on the transglycosylation behavior. The formation of the corresponding CD-based oligosaccharide clusters from Endo-M was also evaluated.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 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}

{"title":"One step aqueous synthesis of unprotected glycosyl C-sulfonates","authors":"Govind P. Singh ,&nbsp;Flinta E.D. Wilson ,&nbsp;Nathan H. Reid ,&nbsp;Antony J. Fairbanks","doi":"10.1016/j.carres.2025.109411","DOIUrl":"10.1016/j.carres.2025.109411","url":null,"abstract":"<div><div>A one-step reaction for the production of unprotected glycosyl C-sulfonates directly from reducing sugars in aqueous solution has been developed, avoiding the use of any protecting groups. The reaction is equally applicable to disaccharides. The structure of the β-<em>gluco</em> C-sulfonate was confirmed by X-ray crystallography. Investigations showed that it did not inhibit almond β-glucosidase at a concentration of 100 μM.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109411"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143350208","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 and antioxidant evaluation of coumarin-functionalised chitosan: A potent, non-toxic free radical scavenging compound","authors":"Siyu Zhu ,&nbsp;Qin Miao ,&nbsp;Qiuhong Chen ,&nbsp;Liguang Tian ,&nbsp;Fang Dong ,&nbsp;Zhanyong Guo ,&nbsp;Qing Li","doi":"10.1016/j.carres.2024.109311","DOIUrl":"10.1016/j.carres.2024.109311","url":null,"abstract":"<div><div>In the present study, we designed to link the coumarin molecule to chitosan via a triazole group and synthesized chitosan-coumarin derivatives, which were further quaternized in one step in order to further improve their solubility to obtain a second series of chitosan-coumarin ammonium salt derivatives. The structures of these chitosan derivatives were verified by FT-IR and ¹H NMR. They were tested for their antioxidant activities. The experimental results showed that the derivatives had excellent free radical scavenging ability. The introduction of the coumarin moiety significantly improved the antioxidant activity, and the scavenging capacity was much higher than that of the chitosan feedstock in all three antioxidant tests. Overall, the scavenging capacity of chitosan-coumarin ammonium salt derivatives was slightly higher than that of chitosan-coumarin derivatives, with the highest scavenging rates in all three tests. Compound 8B scavenged 98.74 % (0.01 mg/mL) of superoxide anion radicals, compound 8D scavenged 95.5 % (0.3 mg/mL) of DPPH radicals and compound 8A scavenged 92.97 % (0.2 mg/mL) of hydroxyl radicals. Toxicity assays used L929 cells demonstrated that there was no significant toxicity of the derivatives. The results indicated that the chitosan derivatives described herein were safe and non-toxic and have good antioxidant activity.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 109311"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142791033","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}