Carbohydrate Research最新文献

{"title":"Chitin recognition by a periplasmic chitooligosaccharide-binding protein from Vibrio cholerae","authors":"Takayuki Ohnuma ,&nbsp;Teruki Yoshimoto ,&nbsp;Wipa Suginta ,&nbsp;Tamo Fukamizo","doi":"10.1016/j.carres.2025.109552","DOIUrl":"10.1016/j.carres.2025.109552","url":null,"abstract":"<div><div>The mechanism of chitin recognition by a periplasmic chitooligosaccharide-binding protein from Vibrio cholerae (VcCBP) was studied by thermal shift assays and isothermal titration calorimetry using di-N-acetylchitobiose, (GlcNAc)2; mono-N-acetylchitobioses, GlcN-GlcNAc and GlcNAc-GlcN; and fully de-N-acetylated chitobiose, (GlcN)2; as the ligands. As judged from the thermal shifts (ΔTm) of VcCBP upon the addition of individual chitobioses, the binding abilities toward VcCBP appeared to decrease in the order of (GlcNAc)2 &gt; GlcN-GlcNAc &gt; GlcNAc-GlcN ≫ (GlcN)2. Although the de-N-acetylation effect of the reducing end GlcNAc was more significant than that of the non-reducing end, both N-acetyl groups were found to cooperatively contribute to the interaction between VcCBP and (GlcNAc)2. The binding affinity of GlcN-GlcNAc to VcCBP was lower than that of (GlcNAc)2 by only 0.5 kcal·mol-1 of ΔG°; however, the entropy gain (-TΔS°) was enhanced in the former compared with the latter. GlcN-GlcNAc are likely to bind loosely to VcCBP but unlikely to undergo translocation by the VcCBP-mediated transporter system.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109552"},"PeriodicalIF":2.4,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144147534","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":"A new type of cationic surfactant prepared by surface modification on sucrose carbon dots via an entirely green approach and the inhibition on growth of E. coli and S. aureus","authors":"Jian Yang,&nbsp;Xiang Liu","doi":"10.1016/j.carres.2025.109541","DOIUrl":"10.1016/j.carres.2025.109541","url":null,"abstract":"<div><div>Sucrose was renewable resource which was a raw material for preparing carbon dots (CDs) since it was readily to be carbonized. Chemical modification could realize a tremendous change of the performance of the CDs. A novel technique of preparing a new type of cationic surfactant derived from sucrose CDs (SCDs) was described herein in detail. Firstly, SCDs were prepared via a hydrothermal treatment of 180° on the mixture of 1.0 g aqueous sucrose solution and 200 μL hydrogen peroxide for 2.0 h. Then SCDs were modified chemically by virtue of reflux heating on mixture of SCDs and <em>n</em>-dodecylamine in aqueous medium for realizing chemical bonding between hydrophobic hydrocarbon chain in <em>n</em>-dodecylamine and SCDs (represented with SCDs-C12). SCDs-C12 declined surface tension of water from 72.0 to 32.9 mN m⁻¹ which was comparable to several traditional surfactants or novel cationic surfactants. Moreover, any organic solvent was never used in the whole procedure. Zeta potential measurement indicated SCDs-C12 was positive charged which declared SCDs-C12 belonged to cationic surfactant. Antibiosis experiments demonstrated SCDs-C12 performed wonderfully in inhibiting the growth of <em>E</em>. <em>coli</em> and <em>S</em>. <em>aureus</em>. Thus we provided a green chemical approach of preparing a new type of cationic surfactant with inexpensive raw material.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109541"},"PeriodicalIF":2.4,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144106146","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":"Extraction, structural characterization, and bioactivity of laminarin and fucoidan from brown macroalgae Chorda filum","authors":"Ashok S. Jagtap,&nbsp;Archana Singh,&nbsp;Anand Jain","doi":"10.1016/j.carres.2025.109551","DOIUrl":"10.1016/j.carres.2025.109551","url":null,"abstract":"<div><div>The present study investigates the structural characterization and bioactivity of macroalgal polysaccharides (laminarin and fucoidan) extracted and purified from <em>Chorda filum</em> collected from Kongsfjorden, Arctic. The extraction was done using a hydrothermal-assisted extraction method followed by purification using ion exchange and size-exclusion chromatography. Two purified fractions, <em>Chorda</em> purified fraction (CPF) 1 (neutral) and CPF 2 (anionic), were obtained and examined for their bioactivity and chemical characterization. The major fraction CPF1 displayed notable free radical inhibition activities: 1, 1-diphenyl-2-picryl-hydrazyl (IC₅₀ 5.21 ± 0.24 mg mL⁻¹), 2, 2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (IC₅₀ 3.28 ± 0.04 mg mL⁻¹), and hydrogen peroxide (IC₅₀ 3.06 ± 0.12 mg mL⁻¹). It also exhibited strong α-glucosidase enzyme inhibition activity (IC₅₀ 0.125 ± 0.012 mg mL⁻¹), equivalent to the model commercial compound acarbose. Fourier-transform infrared (FTIR) analysis of CPF1 indicated O–H, C–H, C<img>O, C–C, and C–O stretching, reflected by peaks at 3335 cm⁻¹, 2919 cm⁻¹, 1369 cm⁻¹, 1100 cm⁻¹, and 1030 cm⁻¹, respectively. The monosaccharide composition CPF1 revealed a major composition of glucose with mannitol residues. The 1H Nuclear magnetic resonance (NMR) peaks at <em>δ</em> 3.3–3.6 ppm, <em>δ</em> 3.5–3.7 ppm, <em>δ</em> 3.6–3.9 ppm, <em>δ</em> 4.3–4.5 ppm, <em>δ</em> 4.6–4.8 ppm and <em>δ</em> 5.1–5.3 ppm and 13C NMR spectrum peak at δ60.66, 68.08, 73.28, 75.60, 84.11, and 102.5 ppm corresponded to C6, C4, C5, C2, C3, and C1 of m-type β-(1, 3)-glucan structure. The molecular mass of CPF1 using gel permeation chromatography (GPC) was found to be approximately 64 kDa. In summary, CPF1, a bioactive, m-type laminarin, was successfully extracted and purified from the understudied filamentous macroalgae <em>C. filum</em>.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109551"},"PeriodicalIF":2.4,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144116058","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":"Molecular weight determination by Chromatography and Viscometry: A case study using novel polysaccharide of Eupatorium adenophorum L","authors":"Sushil Bhattarai,&nbsp;Vineet Kumar","doi":"10.1016/j.carres.2025.109542","DOIUrl":"10.1016/j.carres.2025.109542","url":null,"abstract":"<div><div>Molecular weight analysis of natural polysaccharides is necessary for diverse nutraceutical, pharmaceutical, biological, chemical and other industrial applications. The present study focuses on the determination of the molecular weight of polysaccharide from <em>Eupatorium adenophorum</em> using HP-GPC and Viscometry independently, apart from the chemical composition of constituent monosaccharides. The novel polysaccharide was isolated from leaves of the species, followed by purification using repetitive precipitation, centrifugation, dialysis and chromatographic purification to obtain the polysaccharide in 0.62 ± 0.08 % yield. To analyze monosaccharides constituting polysaccharide, it was hydrolyzed, followed by reduction of hydrolysates and derivatization to corresponding alditol acetates by acetylation. Weight average and number average molecular weights were determined by chromatography (HPGPC) with the help of known MW dextran standards. The viscosity average molecular weight was determined by intrinsic viscosity measurement using the Ubbelohde dilution viscometer and applying the Mark-Houwink equation. GC-MS/FID analysis indicated the presence of <span>l</span>-arabinose, <span>d</span>-xylose, <span>d</span>-mannose, <span>d</span>-glucose and <span>d</span>-galactose as the constituent monosaccharides in 1.61:1.00:0.25:5.89:3.24 M ratios. The different molecular weights were determined to be 4.05 × 10⁵ Da (M_W), 2.28 × 10⁵ Da (M_N) and 3.59 × 10⁵ Da (M_<em>ƞ</em>). The polysaccharide has a polydisperse nature with PDI value of 1.793. Such prudent studies are useful for third-world countries and undergraduate laboratories requiring the guided molecular weight-based screening for diverse applications, but do not have HPGPC in the laboratory. Results indicate that a simple glass Ubbelohde Dilution Viscometer fulfils the goal of molecular weight determination. The molecular weight and monosaccharide composition of <em>E. adenophorum</em> leaf polysaccharide have been reported for the first time.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109542"},"PeriodicalIF":2.4,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144106223","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":"Amidated xanthan gum-coated gastroretentive beads for controlled release of chebulinic acid solid dispersions","authors":"Bigul Yogeshver Bhardwaj ,&nbsp;Uma Ranjan Lal ,&nbsp;Ram Prakash Dwivedi ,&nbsp;Jen Chang Yang ,&nbsp;Poonam Negi","doi":"10.1016/j.carres.2025.109528","DOIUrl":"10.1016/j.carres.2025.109528","url":null,"abstract":"<div><div>This study investigates the usefulness of chemically modified xanthan gum (XG), a natural polysaccharide known for its mucoadhesive and swelling characteristics, in gastroretentive drug delivery systems. XG was modified through amidation using triethanolamine in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) as a coupling agent. The resulting amidated xanthan gum (AXG) exhibited significantly improved physicochemical properties, including reduced hydrophilicity, enhanced thermal stability, and increased crystallinity, as confirmed by FTIR, DSC, XRD, and ^1H NMR analyses. Sodium alginate beads were prepared via the ionotropic gelation and subsequently coated with XG and AXG through diffusion-controlled interfacial complexation. The formulations demonstrated sustained drug release (74.8–93.1 %), low densities (0.524–0.40 g/cm³), minimal lag time (5.12–6.18 s), and high drug encapsulation efficiency (58.01–66.43 %). AXG-coated formulations exhibited a higher swelling index (161 %) compared to XG-coated formulations (119 %). SEM analysis revealed the presence of AXG fragments on the bead surfaces. <em>Ex vivo</em> studies confirmed superior mucoadhesive properties of AXG (58 %) compared to XG (46 %). In conclusion, AXG-based composites outperformed XG in achieving targeted and controlled drug delivery to the stomach.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109528"},"PeriodicalIF":2.4,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144099649","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":"Corrigendum to “Synthesis of a fluorescent analog for exploring the functions of the bacterial glycopyrophospholipid MPIase” [Carbohydrate Res. 553 (2025) 109483]","authors":"Tsukiho Osawa ,&nbsp;Kaoru Nomura ,&nbsp;Keiko Shimamoto ,&nbsp;Kohki Fujikawa","doi":"10.1016/j.carres.2025.109514","DOIUrl":"10.1016/j.carres.2025.109514","url":null,"abstract":"","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109514"},"PeriodicalIF":2.4,"publicationDate":"2025-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144101451","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":"Bi(OTf)3-promoted direct activation of formidable per-O-acetylated ʟ-rhamnose Donor: Stereoselective access to α-ʟ-rhamnopyranosides","authors":"Ankit Yadav,&nbsp;Nitin Kumar,&nbsp;Sudhir Kashyap","doi":"10.1016/j.carres.2025.109527","DOIUrl":"10.1016/j.carres.2025.109527","url":null,"abstract":"<div><div>Rare ʟ-hexoses, including deoxy ʟ-hexoses, serve as potential chemical probes for carbohydrate-based drug discovery and vaccine development. 6-Deoxy sugars, particularly ʟ-rhamnose, are essential components of bacterial surface glycans, playing a key role in pathogen-host cell recognition and various physiological functions. Herein, we present an alternative and highly efficient ʟ-rhamnosylation utilizing the milder oxo-philic Bi(OTf)₃ as the promoter, enabling the assembly of biologically significant <em>α</em>-ʟ-rhamnopyranosides in good yields. The Bi-mediated direct anomeric activation of peracetylated ʟ-rhamnose (ʟ-Rha) is amenable to a wide range of acceptors, including sugars, amino acids, natural products, and bioactive scaffolds. The stereocontrolled glycosylation offers significant advantages, utilizing greener catalysts and atom-economical transformations, avoiding expensive ligands/additives, and tolerating the diverse functional groups.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109527"},"PeriodicalIF":2.4,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144135097","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":"A brief account of the application of glycosyl halide as glycosyl radical precursor towards glycosylation through visible light catalysis","authors":"Ramanand Das ,&nbsp;Rahul Haldar ,&nbsp;Irshad Ahmad Zargar ,&nbsp;S.K. Bappa ,&nbsp;Taraknath Kundu ,&nbsp;Debaraj Mukherjee","doi":"10.1016/j.carres.2025.109537","DOIUrl":"10.1016/j.carres.2025.109537","url":null,"abstract":"<div><div>Glycosylation is potentially one of the most important reactions in glycochemistry, where precise control over the anomeric selectivity is crucial for synthesizing biologically relevant glycoconjugates. Over the last two decades, the advent of visible light chemistry for the generation of glycosyl radicals and its application in the synthesis of glycosides has revolutionized the impact on the stereoselectivity of glycosylation. The visible light-driven radical-based reactions offer exceptional functional group tolerance, operate under mild reaction conditions, and have emerged as a powerful tool for synthesizing potent glycosyl compounds, which include aryl/alkyl glycosides, 2-deoxy sugar, glycosylamino acid, glycosylpeptides, and other glyco-conjugates. In this review article, a brief account of the evolution of glycosyl radical chemistry, with a focus on the visible light-mediated activation of glycosyl halides and its transformative impact on glycoside synthesis, has been discussed.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109537"},"PeriodicalIF":2.4,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144116002","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":"A new polysaccharide from fruit bodies of Morchella elata: Chemical structure and immunomodulation abilities","authors":"Gopal De ,&nbsp;Debsankar Das ,&nbsp;Andreas Koschella ,&nbsp;Sanhita Ghosh ,&nbsp;Chiranjib Pal","doi":"10.1016/j.carres.2025.109529","DOIUrl":"10.1016/j.carres.2025.109529","url":null,"abstract":"<div><div>A new polysaccharide (MEPS, <em>Morchella elata</em> polysaccharide) obtained through alkali extraction from fruit bodies of <em>Morchella elata</em> was purified by dialysis and sepharose-6B column chromatography. Chemical and spectroscopic analysis including GLC, GLC-MS, FT-IR, 1D NMR (¹H, ¹³C, DEPT-135) and 2D NMR (TOCSY, HMQC, NOESY, DQF, ROESY, and HMBC) revealed that the backbone of its repeating unit was →6)-β-<span>d</span>-Man<em>p-</em>(1 → 3)-α-<span>d</span>-Glc<em>p</em>-(1 → 4)-α-<span>d</span>-Glc<em>p-</em>(1→, branched at C-3 of (1 → 4)-linked- α-<span>d</span>-Glc<em>p</em> by α-<span>d</span>-Man<em>p-</em>(1 → 4)-α-<span>d</span>-Glc<em>p-</em>(1 → 4)-α-<span>d</span>-Gal<em>p-</em>(1 → . It was also found that a terminal β-<span>l</span>-fucopyranosyl residue was attached at C-3 of α-<span>d</span>-glucopyranosyl residue of the branched chain. <em>In vitro</em> evaluation of immune modulation of the polysaccharide revealed the significant macrophage polarizing properties and capability to induce an alternative phenotype M2 in peritoneal macrophages obtained from BALB/c mice. It was further confirmed by the ability to induce the expression of M2 polarizing cytokines, specifically IL-10.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109529"},"PeriodicalIF":2.4,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144106145","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":"Re-evaluating adenosine-nucleoside polyphosphate levels in human cells by mass spectrometry","authors":"Elrike R. Reinalter ,&nbsp;Jakob Arnold ,&nbsp;Jakob Zwicker,&nbsp;Andreas Marx","doi":"10.1016/j.carres.2025.109518","DOIUrl":"10.1016/j.carres.2025.109518","url":null,"abstract":"<div><div>Dinucleoside polyphosphates (Np_nNs) are known as alarmones but their functions in cellular metabolism remain largely unexplored till to date. Here, we report new data concerning their cellular quantification using mass spectrometry-based methods. Key for this approach were ¹³<em>C</em>-isotope-labeled internal standards of eight different compounds (¹³<em>C</em>-<strong>A</strong>p_n<strong>N</strong>, n = 3,4; <strong>N</strong> = <strong>A</strong>denosine, <strong>C</strong>ytidine, <strong>G</strong>uanosine, <strong>U</strong>ridine) that were chemically synthesized from ¹³<em>C</em>₅-adenosine. For this, a novel synthesis strategy was developed. These compounds were used to account for losses during the extraction for the determination of intracellular Ap_3/4N-levels. Cell samples from two human cell lines, HEK293T and H1299, were measured using a triple quad mass spectrometer (TQ-MS). Additionally, menadione was added to the cell dishes to generate oxidative stress. We were able to reproduce previous findings that all Ap_3/4N levels increase in stressed cells. In addition, we showed that cells lacking the Np₃N hydrolase Fhit (fragile histidine triad) (H1299, FHIT-negative) exhibit hundred-fold increased levels of Ap₃Ns but also ten-fold increased levels of Ap₄Ns. This finding contradicts previous data, where no impact of the expression of Fhit on Ap₄N-levels was detected. For FHIT-negative cells, no significant increase in Ap_3/4N levels was observed when oxidative stress was applied, suggesting that a change in hydrolase activity could be the primary stress response rather than increased biosynthesis.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"554 ","pages":"Article 109518"},"PeriodicalIF":2.4,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124567","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}