{"title":"Forewords for the special issue of the National Conference on Synthetic Carbohydrate Chemistry","authors":"Jian-Song Sun","doi":"10.1080/07328303.2025.2451823","DOIUrl":"10.1080/07328303.2025.2451823","url":null,"abstract":"","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 4","pages":"Pages 113-114"},"PeriodicalIF":2.2,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145861082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wuxian Zeng , Le Zhang , Jielin Zhao , Longfei Ren , Jiaqi Li , Guofeng Gu
{"title":"Synthesis and immunological study of tetrasaccharide repeating units of capsular polysaccharide of Group B Streptococcus serotype VIII and their protein conjugates","authors":"Wuxian Zeng , Le Zhang , Jielin Zhao , Longfei Ren , Jiaqi Li , Guofeng Gu","doi":"10.1080/07328303.2024.2410793","DOIUrl":"10.1080/07328303.2024.2410793","url":null,"abstract":"<div><div>This study reports the efficient synthesis of three tetrasaccharide derivatives of Group B <em>Streptococcus</em> (GBS) serotype VIII capsular polysaccharide with alternative glycan sequences and spacer chains through a convergent chemical glycosylation manner or a one-pot three-enzyme assembly protocol. Using bifunctional glutarate ester as the linker, these synthesized oligosaccharides were efficiently conjugated with recombinant ScpA193 protein, generating the resultant oligosaccharide-ScpA193 conjugates with desirable carbohydrate loading. ELISA analysis of the antisera obtained from mice inoculated with the synthetic glycoconjugates showed the elicitation of strong oligosaccharide-specific immunoglobulin G (IgG) antibodies, suggesting the potential of the synthesized oligosaccharides for use in the development of GBS vaccines.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 4","pages":"Pages 153-185"},"PeriodicalIF":2.2,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145861081","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hao Gong , Le Zhang , Wenhan Guo , Huixin Qiu , Guangli Yu , Chao Cai
{"title":"Chemical synthesis of a trisaccharide fragment of a fucosylated glucuronomannan isolated from brown algae","authors":"Hao Gong , Le Zhang , Wenhan Guo , Huixin Qiu , Guangli Yu , Chao Cai","doi":"10.1080/07328303.2024.2410797","DOIUrl":"10.1080/07328303.2024.2410797","url":null,"abstract":"<div><div>Fucose is abundant in marine organisms, primarily as fucoidan and fucosylated chondroitin sulfate. Our previous study characterized a sulfated and fucosylated glucuronomannan (SFGM) isolated from marine brown algae, exhibiting notable antiviral activity and potential for drug development. Herein, a trisaccharide fragment of this SFGM in the form of [<em>α</em>-L-Fuc(2, 4-diS)]-(1→3)-<em>α</em>-D-Man-(1→4)-<em>α</em>-D-GlcA-OMP was synthesized for the first time. Stereoselective formation of the <em>α</em>-1,2-<em>cis</em>-fucosidic bond was achieved by leveraging solvent effects. The sulfated trisaccharide as the final product, featuring a 2,4-diS-fucose unit and the <em>p</em>-methoxyphenyl group as a pendant at the anomeric position, was successfully accomplished. The synthetic strategy developed in this study offers a foundation for the pharmaceutical development of these SFGM oligosaccharides.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 4","pages":"Pages 201-221"},"PeriodicalIF":2.2,"publicationDate":"2024-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145861083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tao Xiong , Zhen Cao , Jiarui Gu , Nengzhong Wang , Mingguo Liu , Hui Yao
{"title":"Stereoselective synthesis of 3-sulfone sugars via cobalt catalysis","authors":"Tao Xiong , Zhen Cao , Jiarui Gu , Nengzhong Wang , Mingguo Liu , Hui Yao","doi":"10.1080/07328303.2024.2399506","DOIUrl":"10.1080/07328303.2024.2399506","url":null,"abstract":"<div><div>We report herein the stereoselective synthesis of 3-sulfone sugars in good yields from glycals and sodium arylsulfinates. Various 3,4-<em>O</em>-carbonate glycals were sulfonylated directly by a range of benzene- and naphthalene-sulfinic acid sodium salts catalyzed by cobalt species, demonstrating a broad substrate scope. The mechanism of cobalt-catalyzed decarboxylative allylation from the bottom face of the sugar ring due to the steric effect from the C3 group of glycals was proposed. Moroever, cobalt catalysis tends to favor branched allylation, resulting in excellent regioselectivity. This synthetic strategy features the green sulfone source, good functional group tolerance, exclusive regioselectivity, and excellent stereoselectivity.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 3","pages":"Pages 70-89"},"PeriodicalIF":1.2,"publicationDate":"2024-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142416350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"The impacts of benzoyl and benzyl groups on the non-covalent interactions and electronic properties of glycosyl acceptors","authors":"","doi":"10.1080/07328303.2024.2366770","DOIUrl":"10.1080/07328303.2024.2366770","url":null,"abstract":"<div><div>Modulating the reactivity of glycosyl acceptors has become a key in promoting the chemical synthesis of complex glycans. Herein, computational chemistry was employed to explore the impacts of protecting groups on the non-covalent interactions and electronic properties of glycosyl acceptors. Wavefunction analyses showed that substituting benzoyl groups with benzyl groups and introducing a benzyl group to the C2 amine of a D-Glc<em>p</em>NAc residue can eliminate intra-/intermolecular hydrogen bonds, thereby altering the charge distribution significantly. This protecting group-induced charge distribution increases the nucleophilicity of hydroxyl group. This study may contribute to understanding the assistance of computational chemistry in glycan synthesis.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 3","pages":"Pages 51-69"},"PeriodicalIF":1.2,"publicationDate":"2024-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141341451","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Guozhu Zhang , Yuan Guan , Xin Zhang , Jing Li , Haishan Chen , Li Zhou , Jun Liang , Xia Li
{"title":"Chemical modifications of xylan from sugarcane bagasse and their regulatory effects on gut microbiota in mice","authors":"Guozhu Zhang , Yuan Guan , Xin Zhang , Jing Li , Haishan Chen , Li Zhou , Jun Liang , Xia Li","doi":"10.1080/07328303.2024.2399517","DOIUrl":"10.1080/07328303.2024.2399517","url":null,"abstract":"<div><div>The absorption and metabolism of indigestible dietary glycans play a crucial role in maintaining the integrity of the intestinal barrier and shaping the gut microbiota. Three chemically modified products of xylan, including carboxymethylated xylan, xylan–zinc complex, and carboxymethylated xylan–zinc complex, were synthesized using xylan from sugarcane bagasse. The potential effects of xylan before and after modification on the intestinal barriers and intestinal microbiota of mice were subsequently investigated and compared, revealing distinct changes in the gut microbiota of mice. The results suggest that the chemically modified xylan products have the potential to induce specific regulatory functions on the gut microbiota.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 3","pages":"Pages 90-111"},"PeriodicalIF":1.2,"publicationDate":"2024-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142416349","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of 2,3,4-13C-labeled isoflavone 7-O-glucosides","authors":"Zeguo Fang , Nawaf Al-Maharik","doi":"10.1080/07328303.2024.2366789","DOIUrl":"10.1080/07328303.2024.2366789","url":null,"abstract":"<div><p>The current body of research on the health implications of isoflavone phytoestrogens still presents unsolved matters pertaining to absorption, metabolism, and bioavailability. To conduct research in this particular domain, it is important to possess the means to obtain samples of both isoflavone 7-<em>O</em>-glucosides, which are naturally occurring in plants, and 7-<em>O</em>-glucuronides, which are major metabolites present in mammals. To comprehensively examine the potential health advantages, it is important to precisely measure the concentrations of phytoestrogens present in various food sources and bodily fluids. The use of C-labeled isoflavones was critical to the development of a methodology that allows for precise measurement. 2,3,4-<sup>13</sup>C-Labeled isoflavone 7-<em>O</em>-glucosides, namely 2,3,4-<sup>13</sup>C-labeled daidzin, genestin and glycitin, were efficiently prepared via BF<sub>3</sub>·Et<sub>2</sub>O catalyzed glycosylation at the 7-<em>O</em>-position of <sup>13</sup>C-labeled 4′-<em>O</em>-hexanoyldaidzein, 4′-<em>O</em>-hexanoylglycitein and 5,4′-<em>O</em>-dihexannoylgenestein with 2,2,2-trifluoro-<em>N</em>-(<em>p</em>-methoxyphenyl)acetamidates as glycosyl donors. It was found that protecting all of the OH groups in the isoflavones with hexanoyl groups, with the exception of the 7-OH group, resulted in an increase in both their solubility in organic solvents and the reaction efficiency.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 1","pages":"Pages 37-50"},"PeriodicalIF":1.2,"publicationDate":"2024-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142228943","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Lvfeng Zhang , Youling Liang , Xiaona Li , Rongkun Liu , Jibin Zheng , Peng Xu , Biao Yu , You Yang
{"title":"Insight into gold-catalyzed glycosylation of glycosyl ynenoates","authors":"Lvfeng Zhang , Youling Liang , Xiaona Li , Rongkun Liu , Jibin Zheng , Peng Xu , Biao Yu , You Yang","doi":"10.1080/07328303.2024.2366774","DOIUrl":"10.1080/07328303.2024.2366774","url":null,"abstract":"<div><p>Gold-catalyzed glycosylation using alkyne donors is a versatile approach for the efficient assembly of diverse types of glycosides due to its catalytic and mild glycosylation properties. Minor structural alterations might significantly affect the glycosylation reaction when the alkyne-based leaving groups are simplified. By mapping the glycosylation reactivities of a series of structurally simplified alkyne donors, herein we demonstrate the role of each characteristic functional group of glycosyl ynenoates. Based on the isolation and the X-ray diffraction characterization of the pyran-5-ylgold(I) complex generated from the leaving group, a plausible mechanism of the gold(I)-catalyzed glycosylation with glycosyl ynenoates as donors was proposed.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 1","pages":"Pages 21-36"},"PeriodicalIF":1.2,"publicationDate":"2024-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142229041","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of glycosylphosphatidylinositol analogues with an unnatural β-D-glucosamine-(1→6)-myo-inositol motif","authors":"","doi":"10.1080/07328303.2024.2343004","DOIUrl":"10.1080/07328303.2024.2343004","url":null,"abstract":"<div><p>Glycosylphosphatidylinositol (GPI) anchors contain a unique α-D-glucosamine-(1→6)-<em>myo</em>-inositol [αGlcN(1,6)Ins] motif in their conserved core structure. To facilitate investigations of the functional roles of this structural motif, two GPI analogues containing unnatural βGlcN(1,6)Ins, instead of αGlcN(1,6)Ins, and an alkyne group at different positions of the GPI core were designed and synthesized. To this end, an orthogonally protected pseudopentasaccharide derivative of GPIs with the βGlcN(1,6)Ins motif was convergently constructed via [3 + 2] glycosylation and used as the common intermediate to prepare both GPI analogues by streamlined synthetic protocols. The pseudopentasaccharide intermediate and developed protocols can be widely applicable to access various GPI analogues with the βGlcN(1,6)Ins motif. The target GPI analogues contain an alkyne, which allows their further modification to introduce various molecular labels via click chemistry, making them useful probes for the study of GPI anchorage. The differences in reactivity and NMR behavior of the two GPI analogues, as well as the differences of these analogues from previously reported GPI derivatives of similar structure containing an αGlcN(1,6)Ins motif, suggest that the 2-O-phosphoethanolamine moiety on mannose-I and the linkage form of GlcN in GPIs can have a decisive impact on the structure, which is likely relevant to biology.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"43 1","pages":"Pages 1-20"},"PeriodicalIF":1.2,"publicationDate":"2024-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140666500","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wenqiang Liu , Pan He , Shiying Shang , Zhongping Tan
{"title":"Approaches related to the synthesis of Fmoc-Ser/Thr[GalNAc(Ac)3-α-D]-OH","authors":"Wenqiang Liu , Pan He , Shiying Shang , Zhongping Tan","doi":"10.1080/07328303.2024.2333417","DOIUrl":"10.1080/07328303.2024.2333417","url":null,"abstract":"<div><div>Protein <em>O</em>-glycosylation, particularly mucin-type glycosylation, plays important biological roles. However, the limited access to homogeneously glycosylated protein isoforms (glycoforms) has impeded the establishment of correlations between diverse glycan structures and protein properties, restricting therapeutic and diagnostic applications. Chemical synthesis of glycopeptides utilizing properly protected glycoamino acids as building blocks has emerged as a valuable approach to address the gap in glycoform acquisition. This review focuses on past efforts for the chemical synthesis of two fundamental glycoamino acid building blocks, Fmoc-Ser[GalNAc(Ac)<sub>3</sub>-α-D]-OH and Fmoc-Thr[GalNAc(Ac)<sub>3</sub>-α-D]-OH, by categorizing various methods based on glycosylation donors. The emphasis is on stereoselectivity, synthetic route length, and overall yield, with the goal of inspiring and guiding future research to further improve their synthetic efficiency and promote advancements in protein glycosylation studies and applications.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 7","pages":"Pages 223-251"},"PeriodicalIF":1.2,"publicationDate":"2023-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140753467","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}