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Silver trifluoromethanesulfonate as a new efficient catalyst for glycosylation reactions using 2-alkoxy-glyco-[2,1-d]-2-oxazoline glycosyl donors, contributing to the suppression of side reactions of intermolecular aglycon transfer and polymerization of oxazoline derivatives of sugars
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-04 DOI: 10.1016/j.carres.2025.109452
Sergey S. Pertel
{"title":"Silver trifluoromethanesulfonate as a new efficient catalyst for glycosylation reactions using 2-alkoxy-glyco-[2,1-d]-2-oxazoline glycosyl donors, contributing to the suppression of side reactions of intermolecular aglycon transfer and polymerization of oxazoline derivatives of sugars","authors":"Sergey S. Pertel","doi":"10.1016/j.carres.2025.109452","DOIUrl":"10.1016/j.carres.2025.109452","url":null,"abstract":"<div><div>The use of silver trifluoromethanesulfonate as a catalyst for glycoside synthesis using 2-(2,2,2-trichloroethoxy)-2-oxazoline glycosyl donors with d-gluco and <span>d</span>-galacto configuration has been studied. Silver trifluoromethanesulfonate allows the glycosylation reaction to be carried out under very mild conditions in a neutral medium, similar to the <em>sym</em>-collidinium trifluoromethanesulfonate previously used for this purpose. However, compared to <em>sym</em>-collidinium trifluoromethanesulfonate, silver trifluoromethanesulfonate provides better yields of target products and helps to suppress unwanted side reactions such as intermolecular aglycon transfer and polymerization of oxazoline derivatives of sugars. It has been found that the best results of oligosaccharide synthesis are obtained with an equimolar ratio between the glycosyl donor and the catalyst.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109452"},"PeriodicalIF":2.4,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580262","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}
引用次数: 0
Enhanced wound healing and antibacterial efficacy of a novel chitosan quaternary ammonium salt gel incorporating Echinacea purpurea extract
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-02 DOI: 10.1016/j.carres.2025.109445
Shohreh Fahimirad , Mohammadreza Memarzadeh , Hasan Jafari , Morteza Sanagooiezadeh Isfahani , Amir Almasi-Hashiani , Hamid Abtahi
{"title":"Enhanced wound healing and antibacterial efficacy of a novel chitosan quaternary ammonium salt gel incorporating Echinacea purpurea extract","authors":"Shohreh Fahimirad ,&nbsp;Mohammadreza Memarzadeh ,&nbsp;Hasan Jafari ,&nbsp;Morteza Sanagooiezadeh Isfahani ,&nbsp;Amir Almasi-Hashiani ,&nbsp;Hamid Abtahi","doi":"10.1016/j.carres.2025.109445","DOIUrl":"10.1016/j.carres.2025.109445","url":null,"abstract":"<div><div>Wound healing is a complex and dynamic process involving hemostasis, inflammation, proliferation, and remodeling. This study introduces Chitagel, a novel wound-healing gel formulated with 4 % (w/w) chitosan quaternary ammonium salt, 0.1 % (w/w) polyhexamethylene biguanide (PHMB), and 6 % (w/w) <em>Echinacea purpurea</em> extract, designed to provide antibacterial and antioxidant properties. To enhance hydration, 2 % (w/w) dexpanthenol, 10 % (w/w) glycerin, and 4 % (w/w) sorbitol were incorporated as humectants. In vitro analysis demonstrated 92.3 % inhibition of methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) and 89.63 % antioxidant activity via the DPPH assay. Water content analysis confirmed a 62.9 % hydration level, facilitating a moist wound environment. Zeta potential measurement (+44.9 mV) indicated colloidal stability, ensuring sustained antimicrobial activity. In an MRSA-infected rat wound model, Chitagel significantly accelerated wound closure, achieving 82.5 % healing by day 15, compared to 54.3 % in the untreated group. The MTT assay showed enhanced fibroblast proliferation, with 400 μg/mL stimulating the highest cell viability. Histological analysis confirmed improved re-epithelialization, reduced inflammation, and granulation tissue formation. These findings highlight Chitagel as a promising therapeutic for infected wounds, combining antibacterial, antioxidant, and regenerative properties. Further clinical studies are required to validate its efficacy and safety in human applications and to establish its role as a novel wound-healing agent.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109445"},"PeriodicalIF":2.4,"publicationDate":"2025-03-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143600605","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}
引用次数: 0
Corrigendum to “Synthesis and in vitro synergistic antifungal activity of analogues of Panax stipulcanatus saponin against fluconazole-resistant Candida albicans” [Carbohydr. Res. 517 (2022) 108575]
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-03-01 DOI: 10.1016/j.carres.2025.109429
Shan Yin, Li Li, Liuqing Su, Hongfang Li, Yin Zhao, Yandan Wu, Ruina Liu, Fei Zou, Guanghui Ni
{"title":"Corrigendum to “Synthesis and in vitro synergistic antifungal activity of analogues of Panax stipulcanatus saponin against fluconazole-resistant Candida albicans” [Carbohydr. Res. 517 (2022) 108575]","authors":"Shan Yin,&nbsp;Li Li,&nbsp;Liuqing Su,&nbsp;Hongfang Li,&nbsp;Yin Zhao,&nbsp;Yandan Wu,&nbsp;Ruina Liu,&nbsp;Fei Zou,&nbsp;Guanghui Ni","doi":"10.1016/j.carres.2025.109429","DOIUrl":"10.1016/j.carres.2025.109429","url":null,"abstract":"","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109429"},"PeriodicalIF":2.4,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143536595","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}
引用次数: 0
Regioselective O-arylation of 6-hydroxy groups in carbohydrates
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-28 DOI: 10.1016/j.carres.2025.109447
Soumyadip Dey, Shubhi Dwivedi, Abhijit Sau
{"title":"Regioselective O-arylation of 6-hydroxy groups in carbohydrates","authors":"Soumyadip Dey,&nbsp;Shubhi Dwivedi,&nbsp;Abhijit Sau","doi":"10.1016/j.carres.2025.109447","DOIUrl":"10.1016/j.carres.2025.109447","url":null,"abstract":"<div><div>We report an efficient method for regioselective <em>O</em>-arylation of the 6-hydroxy group of carbohydrates. The reaction involves a nucleophilic aromatic substitution reaction (S<sub>N</sub>Ar) using electron-deficient arenes under mild conditions. Regioselectively monoarylated carbohydrate derivative was produced smoothly in the reaction by fine-tuning with the base. The pentafluoropyridine (<strong>P1</strong>) in combination with N, N-diisopropylethylamine (DIPEA) was successfully converted to regioselective <em>O</em>-arylated products of different positional hydroxy group free sugar derivatives with various functional groups.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109447"},"PeriodicalIF":2.4,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143549833","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}
引用次数: 0
Advancement of drugs conjugated with GalNAc in the targeted delivery to hepatocytes based on asialoglycoprotein receptor
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-27 DOI: 10.1016/j.carres.2025.109426
Yafang Zhang , Hongliang Liu , Weina Zhen , Tingting Jiang , Jingxuan Cui
{"title":"Advancement of drugs conjugated with GalNAc in the targeted delivery to hepatocytes based on asialoglycoprotein receptor","authors":"Yafang Zhang ,&nbsp;Hongliang Liu ,&nbsp;Weina Zhen ,&nbsp;Tingting Jiang ,&nbsp;Jingxuan Cui","doi":"10.1016/j.carres.2025.109426","DOIUrl":"10.1016/j.carres.2025.109426","url":null,"abstract":"<div><div>The asialoglycoprotein receptor (ASGPR) is specifically expressed in hepatocytes. Sugar molecules, such as asialoglycoprotein, galactose, galactosamine, and N-acetyl galactosamine (GalNAc), have a high affinity for ASGPR. This review summarizes the structure of ASGPR, the distribution of this molecule in different cells, and the factors influencing the binding of GalNAc to ASGPR. We introduce the application of GalNAc in targeted delivery into hepatocytes by forming conjugated compounds with RNAs and small molecules, and the standard methods for synthesizing GalNAc are also briefly presented. This is to provide an overview of the current research on GalNAc and to shed light on the design of the new GalNAc.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109426"},"PeriodicalIF":2.4,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580261","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}
引用次数: 0
About the assessment of the degree of oxidation of cellulose during periodate reaction: Comparison of different characterization techniques and their discrepancies
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-25 DOI: 10.1016/j.carres.2025.109438
Lorette Brault , Nathalie Marlin , Gérard Mortha , Jérémy Boucher , Dominique Lachenal
{"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, <sup>13</sup>C 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}
引用次数: 0
Synthesis of aryl thioglycosides by metal-free arylation of glycosyl thiols with diaryliodonium salts under basic conditions
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-24 DOI: 10.1016/j.carres.2025.109437
Anand Gaurav , Pintu Kumar Mandal
{"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 Cs<sub>2</sub>CO<sub>3</sub> 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}
引用次数: 0
Photochemical transformations of glycosyl bromides in the presence of amines
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-22 DOI: 10.1016/j.carres.2025.109436
Ziyi Yu , Daichi Inoue , Naoya Sawada , Hiryu Takinami , Titli Ghosh , Norihiko Sasaki , Manabu Abe , Tsuyoshi Taniguchi , Takashi Koike , Toshiki Nokami
{"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}
引用次数: 0
Biosynthesis of Salmonella O43 and Escherichia coli O86 antigens: Comparison of α1,3-GalNAc-transferases WfbG and WbnH
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-22 DOI: 10.1016/j.carres.2025.109434
D. Falconer, K. Phillippopoulos, D. Czuchry, A. Kocev, I. Brockhausen
{"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}
引用次数: 0
N-nitrosamine directed stereoselective O-glycosylation reactions of 2-amino thioglycosides with NIS-TfOH
IF 2.4 3区 化学
Carbohydrate Research Pub Date : 2025-02-21 DOI: 10.1016/j.carres.2025.109435
Vimlesh Kumar Kanaujiya , Chian-Hui Lai , Jeyakumar Kandasamay
{"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}
引用次数: 0
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