Carbohydrate Research最新文献

{"title":"About the assessment of the degree of oxidation of cellulose during periodate reaction: Comparison of different characterization techniques and their discrepancies","authors":"Lorette Brault ,&nbsp;Nathalie Marlin ,&nbsp;Gérard Mortha ,&nbsp;Jérémy Boucher ,&nbsp;Dominique Lachenal","doi":"10.1016/j.carres.2025.109438","DOIUrl":"10.1016/j.carres.2025.109438","url":null,"abstract":"<div><div>This study focuses on the side reactions responsible for the low efficiency of the periodate-chlorite oxidation sequence of cellulose. Discrepancies are systematically observed between different commonly-used characterization methods for assessing the degree of oxidation (DO) of cellulose. Indeed, the different titration methods of the aldehyde groups found in the dialdehyde cellulose (DAC) generated by the Malaprade reaction on cellulose, do not generally fit the titration of the carboxyl groups found in the dicarboxycellulose (DCC), generated after chlorite oxidation of the DAC. Possible side reactions affecting the Malaprade and chlorite reactions, or affecting the accuracy of the titrations, are presented here and discussed. Studying periodate consumption, iodate generation, organic acids release during the reactions, fiber mass yield, sodium hydroxide consumption during the β-alkoxy-elimination reaction of DAC, ¹³C NMR spectra of DAC and DCC, and carboxyl titration of DCC, allowed to conclude that chlorite did not fully oxidize the aldehyde groups in the DAC, but only about one aldehyde out of two. It was found that the non-oxidized aldehydes in the DAC were hindered by hemiacetal-type linkages. This study refutes several well-established hypotheses from the literature when applied to reactions under mild conditions.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109438"},"PeriodicalIF":2.4,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143520179","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":"Synthesis of aryl thioglycosides by metal-free arylation of glycosyl thiols with diaryliodonium salts under basic conditions","authors":"Anand Gaurav ,&nbsp;Pintu Kumar Mandal","doi":"10.1016/j.carres.2025.109437","DOIUrl":"10.1016/j.carres.2025.109437","url":null,"abstract":"<div><div>Herein, we demonstrate the application of unsymmetrical iodonium salts towards <em>S</em>-arylation of glycosyl thiols under metal-free conditions, affording a various stereoretentive thioarylglycosides in moderate to good yields. The application of an inorganic base Cs₂CO₃ enables the C–S bond formation under mild and experimentally simple conditions at room temperature. The proper choice of auxiliary of the unsymmetrical iodonium salt enables the access to diverse functionalized aryl moieties including biphenyl groups and its incorporation into thioarylglycosides.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109437"},"PeriodicalIF":2.4,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143508769","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":"Photochemical transformations of glycosyl bromides in the presence of amines","authors":"Ziyi Yu ,&nbsp;Daichi Inoue ,&nbsp;Naoya Sawada ,&nbsp;Hiryu Takinami ,&nbsp;Titli Ghosh ,&nbsp;Norihiko Sasaki ,&nbsp;Manabu Abe ,&nbsp;Tsuyoshi Taniguchi ,&nbsp;Takashi Koike ,&nbsp;Toshiki Nokami","doi":"10.1016/j.carres.2025.109436","DOIUrl":"10.1016/j.carres.2025.109436","url":null,"abstract":"<div><div>Photochemical transformations of glycosyl bromides are investigated in the presence of amines. The choice of amines such as <em>N</em>,<em>N</em>-diisopropylethylamine and triphenylamine was found to be critical for product selectivity. Alkylation and alkenylation of anomeric carbon with 1,1-diphenylethene could be realized. Triphenylamine also acts as a photocatalyst for alkenylation in the presence of potassium carbonate.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109436"},"PeriodicalIF":2.4,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143508770","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":"Biosynthesis of Salmonella O43 and Escherichia coli O86 antigens: Comparison of α1,3-GalNAc-transferases WfbG and WbnH","authors":"D. Falconer,&nbsp;K. Phillippopoulos,&nbsp;D. Czuchry,&nbsp;A. Kocev,&nbsp;I. Brockhausen","doi":"10.1016/j.carres.2025.109434","DOIUrl":"10.1016/j.carres.2025.109434","url":null,"abstract":"<div><div>Antibiotic resistance is on the rise, making bacterial infections an increasing threat to human health. O-antigenic polysaccharides are important virulence factors of pathogenic Gram-negative bacteria that can be involved in immune evasion and colonization. The O antigens of enteropathogenic <em>Salmonella enterica</em> O43 (SO43) and <em>Escherichia coli</em> O86 (ECO86) are structurally similar and contain a mimic of the blood group B determinant. However, the SO43 O antigen repeating unit has GlcNAc at the reducing end while ECO86 contains a GalNAc residue. To explore this difference we characterized the α1,3-GalNAc-transferase responsible for the addition of GalNAc to GalNAc-PP-undecaprenol in ECO86 (WbnH) and the enzyme proposed to add GalNAc to GlcNAc-PP-undecaprenol in SO43 (WfbG). Substrate specificity study of these GT4 enzymes showed a strict donor specificity for UDP-GalNAc. However, WfbG could use either GlcNAcα- or GalNAcα-PP-phenylundecyl as a natural acceptor substrate analog whereas WbnH was only active with GalNAcα-PP-phenylundecyl. The GlcNAc-PP-undecaprenol 4-epimerase gene in the ECO86 strain can provide the essential acceptor substrate for WbnH. These data help to explain the difference in O antigen structures between SO43 and ECO86. A series of GT4 enzymes was analyzed by bioinformatics to identify common sequences that help to predict their functions. Characterization of these bacterial GTs can identify potential targets to disrupt virulence mechanisms.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109434"},"PeriodicalIF":2.4,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143511927","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":"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}