Carbohydrate Research最新文献

{"title":"N-nitrosamine directed stereoselective O-glycosylation reactions of 2-amino thioglycosides with NIS-TfOH","authors":"Vimlesh Kumar Kanaujiya ,&nbsp;Chian-Hui Lai ,&nbsp;Jeyakumar Kandasamay","doi":"10.1016/j.carres.2025.109435","DOIUrl":"10.1016/j.carres.2025.109435","url":null,"abstract":"<div><div>We described here the stereoselective synthesis of <em>O</em>-glycosides from 2-amino thioglycosides using <em>N</em>-nitrosamine as the directing group. The reaction was activated by using the NIS/TfOH system in dichloromethane at −10 °C. Various sugar and non-sugar acceptors were successfully glycosylated with 2-amino 1-thioglucoside and 2-amino 1-thiogalactoside under mild reaction conditions. These reactions provided β-glycosides in good to excellent yields.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109435"},"PeriodicalIF":2.4,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143474580","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":"Caution, these are glycan sulfates. The features of their interaction with proteins","authors":"Nicolai Bovin ,&nbsp;Marina Sablina ,&nbsp;Galina Pazynina ,&nbsp;Polina Obukhova ,&nbsp;Aligeydar Ragimov ,&nbsp;Nadezhda Shilova","doi":"10.1016/j.carres.2025.109433","DOIUrl":"10.1016/j.carres.2025.109433","url":null,"abstract":"<div><div>In studies of viruses, lectins and especially human blood anti-glycan antibodies using printed glycan array (PGA), sulfated glycans suspiciously often turn out to be the highest-level binders. The binding to sulfated glycan along with parent neutral is easily explained by the similarity of these two glycans, while the unexpected thing is the many times stronger binding. Analysis of data accumulated over almost two decades allows us to explain the observed effect by the Coulomb interaction of the sulfate residue with a positively charged amino acid that accidently appears near the binding site of the neutral glycan backbone. That is, there is an effect of enhancing the specific interaction by an additional electrostatic one. It is expected that the material considered in the article will be useful for the correct interpretation of other data on the specificity of proteins capable of binding charged glycans, which are often encountered in nature.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109433"},"PeriodicalIF":2.4,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143528701","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":"Quaternary ammonium salts of chitosan containing aromatic ring: Synthesis, characterization, antimicrobial, antioxidant and cytotoxicity","authors":"Jingmin Cui ,&nbsp;Yan Sun ,&nbsp;Linqing Wang ,&nbsp;Yuting Ji ,&nbsp;Huishuang Zhao ,&nbsp;Mingzhi Sun ,&nbsp;Zhanyong Guo ,&nbsp;Fang Dong","doi":"10.1016/j.carres.2025.109431","DOIUrl":"10.1016/j.carres.2025.109431","url":null,"abstract":"<div><div>Quaternary ammonium salts of chitosan have been widely used in the development of anti-microbial biomaterials for their important role in inhibiting the growth of microorganisms. However, it is important to modify its structure to obtain more efficient and biologically active derivatives. Herein, a series of chitosan derivatives with antibacterial, antifungal, antioxidant, and non-cytotoxic properties was synthesized. These four quaternary ammonium salts of chitosan were prepared by incorporating 2-thiophenecarboxaldehyde, 2-furancarboxaldehyde, 2-pyridinecarboxaldehyde and benzaldehyde to form Schiff bases, followed by a reductive amination to obtain the chitosan <em>N</em>-derivatives, and quaternized by iodomethane. The inhibition rate of thiophenecarboxaldehyde chitosan trimethyl ammonium iodide (TpTMC) to <em>B. cinerea</em> could reach 93.78 % and the inhibition ability of pyridinecarboxaldehyde chitosan trimethyl ammonium iodide (PyTMC) to <em>F. graminearum</em> could reach 98.08 % at the concentration of 1.0 mg/mL. Furthermore, furancarboxaldehyde chitosan trimethyl ammonium iodide (FrTMC) exhibited a strong ability to scavenge hydroxyl radicals and DPPH radicals, especially the DPPH radicals scavenging ability was comparable to that of <span>l</span>-ascorbic acid at the concentration of 1.6 mg/mL. The B3LYP/6–311++G (d,p) basis set was employed to determine electronic properties, including HOMO-LUMO energies, and to analyze the chemical reactivity of the compounds. L929 cells were used to evaluate the cytotoxicity of the compounds at different concentrations (1−1000 μg/mL). The results demonstrated the diverse applications of aromatic ring-modified quaternary ammonium salts of chitosan, along with their significant antioxidant and antifungal effects against plant fungi. Therefore, these compounds have potential applications in the preparation of agricultural, biological, and medical materials.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109431"},"PeriodicalIF":2.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143487145","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 novel bifunctional type I α-l-arabinofuranosidase of family 43 glycoside hydrolase (BoGH43_35) from Bacteroides ovatus with endo-β-1,4-xylanase activity","authors":"Madhulika Shrivastava ,&nbsp;Aishwarya Aishwarya ,&nbsp;Carlos M.G.A. Fontes ,&nbsp;Arun Goyal","doi":"10.1016/j.carres.2025.109432","DOIUrl":"10.1016/j.carres.2025.109432","url":null,"abstract":"<div><div>The gut bacterium <em>Bacteroides ovatus</em> harbors a diverse arsenal of glycoside hydrolases (GHs), which play pivotal roles in degrading dietary polysaccharides. In this study, we characterized a novel glycoside hydrolase from family 43 and subfamily 35 (<em>Bo</em>GH43_35), cloned from <em>B. ovatus</em>. The 1956 bp gene was expressed in <em>Escherichia coli</em> BL21 (DE3), yielding a homogeneous soluble recombinant enzyme (∼74 kDa) upon purification through immobilized metal-ion affinity chromatography (IMAC). <em>Bo</em>GH43_35 exhibited a remarkable specificity for arabinoxylans, with maximum catalytic activity (4.9 U mg⁻¹) against wheat arabinoxylan (low-viscosity), followed by 3.0 U mg⁻¹ against rye arabinoxylan (high viscosity) and beechwood xylan (2.3 U mg⁻¹). Optimal enzymatic performance was achieved at 37 °C and pH 7.0 having kinetic parameters of <em>V</em>_<em>max</em> 5.7 U mg⁻¹ and <em>K</em>_<em>M</em> calculated to be 2.7 mg mL⁻¹ for wheat arabinoxylan. Notably, <em>Bo</em>GH43_35 retained stability within an acidic pH range (4–5) and displayed a half-life of 89 min at 30 °C. Protein thermal stability assays revealed a melting temperature (<em>T</em>_m) of 41.0 °C. Thin-layer chromatography (TLC) and ¹H NMR analyses of hydrolysed products confirmed the enzyme's dual functionality: an initial α-<span>l</span>-arabinofuranosidase (EC 3.2.1.55) activity, followed by an endo-β-1,4-xylanase (EC 3.2.1.8) activity, as evidenced by the release of xylooligosaccharides, including xylobiose and xylotriose, from xylans. Further structural analysis demonstrated <em>Bo</em>GH43_35's ability to hydrolyze monosubstituted arabinofuranosyl residues from α-1,2- or α-1,3-linked arabinoxylan, confirming its type I α-<span>l</span>-arabinofuranosidase activity. This multifunctional enzyme holds potential in the valorization of hemicellulosic biomass and the production of prebiotic oligosaccharides and other biotechnological applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109432"},"PeriodicalIF":2.4,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143479913","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":"Chemical synthesis of the conjugation-ready tetrarhamnan oligosaccharide of the O-polysaccharide from Azospirillum griseum L-25-5w-1T","authors":"Annesha Dutta,&nbsp;Balaram Mukhopadhyay","doi":"10.1016/j.carres.2025.109430","DOIUrl":"10.1016/j.carres.2025.109430","url":null,"abstract":"<div><div>Synthesis of the tetrarhamnan related to the <em>O</em>-polysaccharide from <em>Azospirillum griseum</em> L-25-5w-1^T is reported. Synthesis of the said structure has been accomplished by convergent [2 + 2]-block synthesis strategy. The target tetrasaccharide in the form of its 3-aminopropyl glycoside is ready for further conjugation with suitable aglycon.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109430"},"PeriodicalIF":2.4,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143454749","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":"Functional characterization of two GH27 ɑ-galactosidases from Penicillium parvum 4–14 and their differential capabilities upon plant biomass degradation","authors":"Wei Wang ,&nbsp;Jiarong Zhu ,&nbsp;Yizhou Wang ,&nbsp;Liangkun Long ,&nbsp;Qunying Lin ,&nbsp;Jing Wang ,&nbsp;Shaojun Ding","doi":"10.1016/j.carres.2025.109428","DOIUrl":"10.1016/j.carres.2025.109428","url":null,"abstract":"<div><div>Two new <em>ɑ</em>-galactosidases PpAgl27B and PpAgl27C from <em>Penicillium parvum</em> 4–14 were functionally investigated in this study. Based on the analysis of catalytic domain and phylogenetic tree, PpAgl27B (435 aa) and PpAgl27C (543 aa) belong to glycoside hydrolase (GH) 27 family. After expression in <em>Pichia pastoris</em>, the recombinant PpAgl27B and PpAgl27C showed the highest activities at pH 3.5 and 65 °C, or 4.0 and 45 °C, respectively. Using <em>p</em>-nitrophenyl-<em>α</em>-<span>d</span>-galactopyranoside (<em>p</em>NPGal) as substrate, the Michaelis constant were 0.90 mM for PpAgl27B and 2.54 mM for PpAgl27C. PpAgl27C had a low catalytic activity toward <em>p</em>NPGal and negligible activities on various natural substrates. Differently, PpAgl27B efficiently released galactose from the artificial substrate, raffinose family oligosaccharides, or galactomannans. Hydrolysis of corn bran arabinoxylan (CBAX) 1 or 2 were conducted by PpAgl27B alone or in combination with the enzyme blend E_CBAX1. PpAgl27B released a small amount of galactose (1.7–3.0 mg/g) from the both substrates. Compared with the individual enzymes, the liberations of galactose, xylose and arabinose from the substrates were significantly enhanced by combing PpAgl27B and E_CBAX1. The degrees of synergy of the enzyme combination for the saccharification of CBAX1 or CBAX2 were 1.20 and 1.13, respectively. PpAgl27B showed promising potential for the valorization of galactose-rich feedstocks as well as CBAX.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109428"},"PeriodicalIF":2.4,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143429077","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 review on the development of sialyltransferase inhibitors","authors":"Xiang Zhang,&nbsp;Xin-Shan Ye","doi":"10.1016/j.carres.2025.109427","DOIUrl":"10.1016/j.carres.2025.109427","url":null,"abstract":"<div><div>Sialylation of terminal glycoconjugates is involved in many important physiological and pathological processes such as tumor metastasis, drug resistance, organismal immunity, and viral infections. Sialyltransferases are enzymes responsible for sialylation modification in organisms, and potent sialyltransferase inhibitors can not only serve as probes for glycobiology studies, but also hold great promise to become agents for tumor therapy and viral infection control in the clinic. This review summarizes the latest progress in the development and application of various sialyltransferase inhibitors. The current challenges and development trends are also discussed.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109427"},"PeriodicalIF":2.4,"publicationDate":"2025-02-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143437024","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":"Theoretical analysis, synthesis and biological activity against normal and cancer cells of a complex formed by a novel sugar cryptand and anticancer drug mitomycin C","authors":"Marta Hoelm ,&nbsp;Stanisław Porwański ,&nbsp;Paweł Jóźwiak ,&nbsp;Anna Krześlak","doi":"10.1016/j.carres.2025.109425","DOIUrl":"10.1016/j.carres.2025.109425","url":null,"abstract":"<div><div>This work presents the theoretical, spectroscopic, and biological characterization of cryptand 1,10-<em>N,N′</em>-bis-(β-<span>d</span>-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane (TN) as a drug carrier for the anticancer agent mitomycin C. Spectroscopic analysis confirms the successful formation of a stable 1:1 complex in water, with the preferred configuration involving interactions between mitomycin C and all functional moieties of TN. These findings are further supported and elaborated upon through theoretical modeling. Using the density functional theory (DFT) method, the complexation energy was estimated at −25.8 kcal/mol (−107.95 kJ/mol). This value is compared with the literature data, accompanied by a detailed discussion. The biological assessment conducted for TN, mitomycin C, and their complex demonstrates that binding mitomycin C in a complex effectively reduces its cytotoxicity toward all analyzed cell lines.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109425"},"PeriodicalIF":2.4,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143429078","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":"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}