Carbohydrate Research最新文献

{"title":"Highly efficient multigram synthesis of 1,4:3,6-Dianhydro-α-D-glucopyranose by chemical synthesis methods: Development and scale-up study of synthetic routes","authors":"Zhi-Fei Chen ,&nbsp;Jia-Ming Zhao ,&nbsp;Hao-Liang Li ,&nbsp;Hao-Yang Chen ,&nbsp;Gao-Lei Xi ,&nbsp;Liu-Ke Zhang ,&nbsp;Qing-Fu Wang ,&nbsp;Qiu-Ling Wang ,&nbsp;Yong-Zhen Zhao ,&nbsp;Kai Yang","doi":"10.1016/j.carres.2025.109402","DOIUrl":"10.1016/j.carres.2025.109402","url":null,"abstract":"<div><div>A reliable chemical synthesis method for the preparation of 1,4:3,6-dianhydro-α-D-glucopyranose (DGP) has been developed on the first time, with an overall four-step yield of 20 % on a 200g scale. The method for 2-OH regioselective benzylation protection of Methyl α-<span>d</span>-glucopyranoside was systematically optimized, providing a more scalable and cost-effective approach. The 3,6-anhydro pyranose intermediate was obtained through a two-step one-pot process. It has been confirmed that 2-OH protection enhanced the ring stability of 3,6-anhydro pyranose and also found that the conformation of 3,6-anhydro pyranose indeed promoted the construction of 1,4-ether bonds. Overall, this work facilitated further application research of DGP in the fields of chemical synthesis, medicinal chemistry, and food chemistry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109402"},"PeriodicalIF":2.4,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143350155","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":"Recombinant expression and characterization of an α-galactosidase from Thermoclostridium stercorarium subsp. thermolacticum DSM 2910 and its application in the hydrolysis of raffinose","authors":"Lin Ge ,&nbsp;Ruobing Jia ,&nbsp;Yingying Liu ,&nbsp;Lingling Zhan","doi":"10.1016/j.carres.2025.109410","DOIUrl":"10.1016/j.carres.2025.109410","url":null,"abstract":"<div><div>Soybean contains anti-nutritional factor raffinose oligosaccharide (RFOs), which can cause flatulence, gastrointestinal dysfunction and low feed utilization rate. However, α-galactosidase can hydrolyze raffinose oligosaccharides (RFOs). Therefore, in this study, a novel α-galactosidase from <em>Thermoclostridium stercorarium subsp. thermolacticum</em> DSM 2910 (TstGal) which can hydrolyze raffinose was cloned, expressed, purified, and characterized. The gene fragment size is 2208 bp, and the enzyme TstGal consists of 736 amino acids. Under the optimum culture conditions, the maximum enzyme activity of the target protein TstGal was 23.8 U/mL. The enzyme was purified 11.3-fold by Ni-NTA agarose resin with an overall recovery of 51.4 % and specific activity of 9.0 U/mg, and its relative molecular weight was about 85 kDa. The optimal temperature of TstGal was 70 °C, and it exhibited excellent thermal stability at 60 °C. Furthermore, The TstGal had the highest activity at pH 6.5 and good pH stability at pH 5.0–7.5. Besides, the enzyme has a good sugar tolerance to galactose and sucrose. In addition, K⁺ and Fe²⁺ could significantly enhance the enzyme activity at a concentration of 5 mM. The values of K_M, V_max, k_cat, and k_cat/K_M for <em>p</em>NPGal were found to be 0.507 mM, 13.979 U/mg, 19.735 s⁻¹, and 38.895 s⁻¹mM⁻¹, respectively. Under the optimum conditions, the maximum hydrolysis rate of raffinose by TstGal reached 99.8 %, which shows that the enzyme had potential application value in food and feed industry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109410"},"PeriodicalIF":2.4,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143073977","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":"Fractionation of the antioxidant (poly)phenol-polysaccharide-protein complex extracted with ammonia from wild blackthorn (Prunus spinosa L.) fruits: structural features of the fractions obtained","authors":"Peter Capek,&nbsp;Iveta Uhliariková,&nbsp;Zuzana Košťáľová","doi":"10.1016/j.carres.2025.109403","DOIUrl":"10.1016/j.carres.2025.109403","url":null,"abstract":"<div><div>Underutilized wild blackthorn fruits are an important source of mainly phenolic compounds, which makes them suitable as potential functional foods supporting human health. The crude polysaccharide complex (Am), isolated from wild blackthorn berries by ammonia, was subjected to ion-exchange chromatography to yield seven fractions differing in the content of carbohydrates, proteins, phenolics and constitutional saccharides. The non-retained fraction, eluted with water, was rich in α-D-glucan, while the fraction eluted with 0.1 M salts had a high xylose content, indicating the presence of a partly acetylated β-D-xylan-type polysaccharides (4-<em>O</em>-methyl-glucuronoxylan, etc.). However, the highest yields were obtained by elution with 0.5 and 0.25 M NaCl and 1.0 M NaOH solutions, while other fractions were low. The two dominant fractions eluted with 0.25 and 0.5 M saline solutions were found to have a high content of GalA and rhamnose, indicating the presence of rhamnogalacturonan (RGI) and 1,4-α-D-homogalacturonan (HG) regions with a low acetyl content and low degree of methyl esterification. The third fraction in terms of yield, eluted with 1.0 M alkali, was a dark brown material with the highest content of phenolic compounds among all fractions. Its carbohydrate portion was rich in glucose, galactose, rhamnose, xylose and arabinose residues, indicating the presence of polysaccharide complex such as α and β-D-glucans, rhamnogalacturonan, arabinan/arabinogalactan and β-D-xylan types of polymers.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109403"},"PeriodicalIF":2.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143073975","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":"Maleimide grafting onto polysaccharides via mild condition esterification and its impact on their structure","authors":"Valentin Silveira ,&nbsp;Mohamed Jebrane ,&nbsp;Adrien Letoffe ,&nbsp;Stergios Adamopoulos","doi":"10.1016/j.carres.2025.109401","DOIUrl":"10.1016/j.carres.2025.109401","url":null,"abstract":"<div><div>This study proposes an innovative approach to tailor the properties of two polysaccharides, microcrystalline cellulose (MCC) and potato starch, through chemical modification in dispersion. The methodology involves the grafting of 6-Maleimidohexanoic acid (6-MHA) moieties onto hydroxyl groups of the polysaccharides without dissolving them in order to keep their native structure preserved. To overcome the slow and inefficient reaction between carboxylic acids of 6-MHA and hydroxyl groups of the polysaccharides, a vinyl ester of 6-MHA was synthesized through the transvinylation of 6-MHA acid with vinyl acetate. The resulting 6-MHA ester was employed to introduce a new functionality to polysaccharides’ hydroxyl groups via transesterification, catalyzed by potassium carbonate. To enhance the reactivity, the polysaccharides were mercerized prior to modification process. The efficiency of the transesterification reaction between the vinyl ester of 6-MHA and the hydroxyl groups of the polysaccharides was confirmed using Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (NMR). Thermal behavior analysis was carried out using thermogravimetric analysis (TGA), while changes in crystallinity resulting from the modification were assessed through X-ray diffraction analysis (XRD). Finally, the impact of the modification on the morphology of polysaccharides was examined with environmental scanning electron microscopy (ESEM). Despite changes in microstructure, MCC kept its macrostructure remained morphologically unchanged while the granular structure of starch was damaged. Maleimide grafting onto MCC and starch has the potential to turn them into thermally reversible materials for various applications such as debondable adhesive or coating.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109401"},"PeriodicalIF":2.4,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143073976","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":"Antimicrobial biodegradable packaging films from phosphorylated starch: A sustainable solution for plastic waste","authors":"Neeru Devi ,&nbsp;Shayoraj ,&nbsp;Geeta ,&nbsp;Shivani ,&nbsp;Simran Ahuja ,&nbsp;Santosh Kumar Dubey ,&nbsp;Sanjay Sharma ,&nbsp;Satish Kumar","doi":"10.1016/j.carres.2025.109404","DOIUrl":"10.1016/j.carres.2025.109404","url":null,"abstract":"<div><div>This study focused on developing biodegradable packaging films based on starch as an alternative to non-biodegradable such as petroleum-derived synthetic polymers. To improve its physicochemical properties, potato starch was chemically modified through phosphorylation. Starch phosphorylation was carried out using cyclic 1,3-propanediol phosphoryl chloride (CPPC), produced phosphorylated starch (PS), and analyzed using Fourier transform infrared (FT-IR), X-ray diffraction (XRD), Nuclear magnetic resonance (NMR), and Thermogravimetric analysis (TGA). The thermal stability of PS increased to 292 °C due to the formation of starch phosphate ester in comparison to pure starch (281 °C). Moreover, using glycerol as a plasticizer, the solvent casting method was employed to synthesize the PS/PVA biofilms. The synthesized biofilms (PPS) were further characterized using FT-IR, TGA, Mechanical testing, and Scanning electron microscopy (SEM). The result indicated that blend films have higher tensile strength (41.61 MPa) and elongation at break (240 %) than pure PVA film (29.84 MPa, 102 %). The soil burial study showed that the biodegradation of PPS blend films increased to 63.79 %. Nevertheless, the blend film showed decreased solubility, water absorption, water vapor transmission rate, and moisture content with PS, while its surface hydrophobicity increased from 61.2° to 95.6°. PPS blends have stronger antibacterial activity against <em>S. aureus</em> than <em>E. coli.</em> Accordingly, the prepared PPS III biofilm was further used for brown bread packaging. Compared to LDPE packaging, the bread wrapped in PPS III blend film exhibited enhanced visual appearance and extended shelf-life. The novelty of our work lies in the modification of starch using CPPC, which was further used to fabricate biodegradable films. Therefore, the developed biofilm may be a reference for additional research and can potentially replace synthetic, non-degradable polymer-based films in the packaging industry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109404"},"PeriodicalIF":2.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143063608","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":"Development and characterization of farnesol complexed in β- and hydroxypropyl-β-cyclodextrin and their antibacterial activity","authors":"Anamaria Mendonça Santos ,&nbsp;Edileuza Marcelo Vieira ,&nbsp;Jemmyson Romário de Jesus ,&nbsp;Cláudio Carvalho Santana Júnior ,&nbsp;José Adão Carvalho Nascimento Júnior ,&nbsp;Ana Maria Santos Oliveira ,&nbsp;Adriano Antunes de Souza Araújo ,&nbsp;Laurent Picot ,&nbsp;Izabel Almeida Alves ,&nbsp;Mairim Russo Serafini","doi":"10.1016/j.carres.2025.109406","DOIUrl":"10.1016/j.carres.2025.109406","url":null,"abstract":"<div><div>Farnesol (FAR) belongs to terpenes group and is a sesquiterpene alcohol and a hydrophobic compound, which can be extracted from natural sources or obtained by organic chemical or biological synthesis. Recent advances in the field of nanotechnology allow the drawbacks of low drug solubility, which can improve the drug therapeutic index. Therefore, this study aimed to prepare the FAR inclusion complexes with β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) through freeze-drying method, proposing their physicochemical characterization, comparing their toxicity, and evaluating their <em>in vitro</em> antibacterial activity. Initially, physical mixture and freeze-dried inclusion complexes of FAR/β-CD and FAR/HP-β-CD were obtained in the molar ratio (1:1). The samples were characterized by DSC, TG/DTG, FTIR, PXRD, SEM, pH_PZC, and the complexation efficiency were performed by HPLC. <em>In vivo</em> toxicity assay was performed using <em>Tenebrio molitor</em> larvae to determine the LD50 and toxic dose of the samples. Also, it was proposed that the evaluation of the fluorescence suppression of Bovine Serum Albumin and the antibacterial activity. The complexation of FAR was evidenced with β-CD and HP-β-CD by the characterization techniques analyzed. The complexation efficiency of FAR/β-CD and FAR/HP-β-CD were 73,53 % and 74.12 %, respectively. The inclusion complexes demonstrated a reduction in toxicity, as evidenced by lower toxic and LD50 doses compared to the free FAR. The inclusion complexes induced conformational changes in BSA, suggesting that they reached the subdomains containing tryptophan residues. In terms of antibacterial activity, FAR/β-CD and FAR/HP-β-CD did not exhibit significant MIC results compared to free FAR, except for FAR/HP-β-CD against <em>S. aureus</em> ATCC 25923.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109406"},"PeriodicalIF":2.4,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045662","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":"New cinnamic acid sugar esters as potential UVB filters: Synthesis, cytotoxicity, and physicochemical properties","authors":"Diego Olivieri ,&nbsp;Michele Verboni ,&nbsp;Serena Benedetti ,&nbsp;Daniele Paderni ,&nbsp;Carla Carfagna ,&nbsp;Andrea Duranti ,&nbsp;Simone Lucarini","doi":"10.1016/j.carres.2025.109405","DOIUrl":"10.1016/j.carres.2025.109405","url":null,"abstract":"<div><div>Cinnamic Acid Sugar Ester Derivatives (CASEDs) are a class of natural compounds that exhibit several interesting biological activities. However, to date, no examples of their use in sunscreen formulations have been reported. Here, we describe the synthesis of a series of novel cinnamic acid esters of glucose (<strong>4a-g</strong>), ribose (<strong>4h</strong>) and lactose (<strong>4i</strong>) starting from the respective acetals <strong>3</strong>. The latter were obtained through oxidative alkoxycarbonylation of olefins. For all compounds <strong>3</strong> and <strong>4</strong>, UV–Vis spectra were recorded and lipophilicity (i.e., clogP) and cytotoxicity were evaluated. All but one of the synthesized compounds were found to be non-cytotoxic at the concentrations tested and, as expected, absorption spectra depended only on the substituents on the aromatic ring. Finally, the <em>ad hoc</em> synthesized compound <strong>3k</strong>, featuring a 4-methoxy substituent on the phenyl ring and a 1,2-<em>O</em>-isopropylidene ribose moiety, provided the most promising results for a possible use as a sunscreen. Indeed, its Sun Protection Factor (SPF), calculated <em>in vitro</em>, was higher with respect to that of ethylhexyl methoxycinnamate (EHMC), which is already utilized in sun care products. Moreover, <strong>3k</strong> showed greater antioxidant properties than EHMC, effectively protecting keratinocytes against H₂O₂-induced oxidative damage. At the same time, it showed no cytotoxic effects and preserved cellular metabolic activity and protein content. Based on these results, we believe that CASEDs could find valid applications in the skincare and cosmetics sectors.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109405"},"PeriodicalIF":2.4,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143051803","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":"Glycans of parasitic nematodes – from glycomes to novel diagnostic tools and vaccines","authors":"Shi Yan","doi":"10.1016/j.carres.2025.109407","DOIUrl":"10.1016/j.carres.2025.109407","url":null,"abstract":"<div><div>Nematodes, commonly known as roundworms, are among the most prevalent and diverse multicellular organisms on Earth, belonging to the large phylum <em>Nematoda</em>. In addition to free-living species, many nematodes are parasitic, infecting plants, animals, and humans. Nematodes possess a wide array of genes responsible for carbohydrate metabolism and glycosylation. The glycosylation processes in parasitic nematodes often result in unique glycan modifications that are not present in their hosts. These distinct glycans can be highly immunogenic to mammalian hosts and play significant immunoregulatory roles during infection. This mini-review article summarises the glycosylation capabilities and characteristics of parasitic nematodes based on glycomic data. It also highlights recent research advances that explore the biological significance of nematode glycans and their potential for diagnostic and vaccine applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109407"},"PeriodicalIF":2.4,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143063642","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":"Efficient synthesis of coumarin based triazole linked O-glycoconjugates as new bio-active glycohybrids","authors":"Sunil Sharma,&nbsp;Ram Sagar","doi":"10.1016/j.carres.2025.109395","DOIUrl":"10.1016/j.carres.2025.109395","url":null,"abstract":"<div><div>Glycohybrids are biologically significant molecules with variety of biological functions and are found as structural motifs in numerous natural products. Here, we report the synthesis of various new coumarin-based <em>O</em>-glycoconjugates as glycohybrids that are chirally enriched and bridged by 1,2,3-triazoles ring system. The1,2,3-triazoles bridging was done via CuAAC click-chemistry. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification, and compatibility with multiple functional groups. Two series of <em>O</em>-glycoconjugates as new glycohybrids were designed and efficiently synthesized in very good isolated yields, using <span>d</span>-glucose, <span>d</span>-galactose, <span>d</span>-mannose, <span>d</span>-arabinose, 3,4,6-tri-<em>O</em>-acetyl-D-glucal, 3,4,6-tri-<em>O</em>-acetyl-D-galactal and 3,4-di-<em>O</em>-acetyl-D-arabinal derived 1-<em>O</em>-propargylated glycosides, reacting with various 4-azidocoumarins under click-chemistry reaction conditions. The prepared new coumarin-based <em>O</em>-glycoconjugates as glycohybrids were found to possess anticancer activity against MCF-7 breast cancer cell lines at micromolar concentration.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109395"},"PeriodicalIF":2.4,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045663","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":"Named reaction in carbohydrate chemistry: A review","authors":"Shakeel Alvi,&nbsp;Rashid Ali","doi":"10.1016/j.carres.2025.109396","DOIUrl":"10.1016/j.carres.2025.109396","url":null,"abstract":"<div><div>Central to the synthetic organic chemist's armoury are the organic/inorganic reagents which are employed to effect a broad range of structural changes. Herein, we report a collection of 29 organic named reactions applicable in the carbohydrate chemistry, arranged in alphabetical order. In this contribution, we have displayed general schemes, examples and probable reaction mechanism for each chemical reaction. This collection should be useful to researchers and students alike.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109396"},"PeriodicalIF":2.4,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143063745","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}