Journal of Carbohydrate Chemistry最新文献

Stereoselective synthesis of 3-sulfone sugars via cobalt catalysis 通过钴催化立体选择性合成 3-砜糖

IF 1.2 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2024-03-23 DOI: 10.1080/07328303.2024.2399506

Tao Xiong , Zhen Cao , Jiarui Gu , Nengzhong Wang , Mingguo Liu , Hui Yao

引用次数: 0

The impacts of benzoyl and benzyl groups on the non-covalent interactions and electronic properties of glycosyl acceptors 苯甲酰基和苄基对糖基受体的非共价相互作用和电子特性的影响

IF 1.2 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2024-03-23 DOI: 10.1080/07328303.2024.2366770

引用次数: 0

Chemical modifications of xylan from sugarcane bagasse and their regulatory effects on gut microbiota in mice 甘蔗渣木聚糖的化学修饰及其对小鼠肠道微生物群的调节作用

IF 1.2 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2024-03-23 DOI: 10.1080/07328303.2024.2399517

Guozhu Zhang , Yuan Guan , Xin Zhang , Jing Li , Haishan Chen , Li Zhou , Jun Liang , Xia Li

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Synthesis of 2,3,4-13C-labeled isoflavone 7-O-glucosides 合成 2,3,4-13C-标记的异黄酮 7-O-葡萄糖苷

IF 1.2 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2024-02-12 DOI: 10.1080/07328303.2024.2366789

Zeguo Fang , Nawaf Al-Maharik

{"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>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-O-glucosides, which are naturally occurring in plants, and 7-O-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. 2,3,4-13C-Labeled isoflavone 7-O-glucosides, namely 2,3,4-13C-labeled daidzin, genestin and glycitin, were efficiently prepared via BF3·Et2O catalyzed glycosylation at the 7-O-position of 13C-labeled 4′-O-hexanoyldaidzein, 4′-O-hexanoylglycitein and 5,4′-O-dihexannoylgenestein with 2,2,2-trifluoro-N-(p-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.</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}

引用次数: 0

Insight into gold-catalyzed glycosylation of glycosyl ynenoates 金催化糖基化乙烯酸盐的深入研究

IF 1.2 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2024-02-12 DOI: 10.1080/07328303.2024.2366774

Lvfeng Zhang , Youling Liang , Xiaona Li , Rongkun Liu , Jibin Zheng , Peng Xu , Biao Yu , You Yang

引用次数: 0

Synthesis of glycosylphosphatidylinositol analogues with an unnatural β-D-glucosamine-(1→6)-myo-inositol motif 具有非天然β-D-氨基葡萄糖-(1→6)-肌醇基团的糖基磷脂酰肌醇类似物的合成

IF 1.2 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2024-02-12 DOI: 10.1080/07328303.2024.2343004

{"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>Glycosylphosphatidylinositol (GPI) anchors contain a unique α-D-glucosamine-(1→6)-myo-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.</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}

引用次数: 0

Efficient synthesis of 2-benzofuranyl C -glycosides by one-pot cascade reaction of sugar alkynes and substituted 2-iodophenols 通过糖炔和取代的 2-碘苯酚的单锅级联反应高效合成 2-苯并呋喃基 C-糖苷

IF 1 4区化学

Journal of Carbohydrate Chemistry Pub Date : 2023-12-10 DOI: 10.1080/07328303.2023.2280538

Z. Cao, Xiang Zhou, Fuyi Zhang, Yufen Zhao

引用次数: 0

Ulvan from green seaweed Ulva lactuca : Optimization of ultrasound-assisted extraction, structure, and cytotoxic activity 绿海藻Ulva lactuca:超声辅助提取、结构及细胞毒活性的优化

4区化学

Journal of Carbohydrate Chemistry Pub Date : 2023-11-14 DOI: 10.1080/07328303.2023.2280560

Thuy T. T. Thanh, Quang V. Ngo, Tai T. Nguyen, Anh N. Nguyen, Thu T. M. Quach, Luong V. Dang, Tam Q. Nguyen, Xuan T. T. Do

{"title":"Ulvan from green seaweed Ulva lactuca : Optimization of ultrasound-assisted extraction, structure, and cytotoxic activity","authors":"Thuy T. T. Thanh, Quang V. Ngo, Tai T. Nguyen, Anh N. Nguyen, Thu T. M. Quach, Luong V. Dang, Tam Q. Nguyen, Xuan T. T. Do","doi":"10.1080/07328303.2023.2280560","DOIUrl":"https://doi.org/10.1080/07328303.2023.2280560","url":null,"abstract":"AbstractAn ulvan was extracted from green seaweed Ulva lactuca by ultrasound-assisted extraction. The extraction conditions were optimized by response surface methodology. The optimal conditions were extraction temperature at 84.75 °C, extraction time of 30.51 min, solvent to material ratio of 60.51 mL/g to achieve the yield of 22.5%. The ulvan is composed of repeated sequences of three disaccharides: →4)-β-D-Glucuronic acid(1→4)α-L-Rhamnose-3-sulfate(1→, →4)α-L-Iduronic acid(1→4)α-L-Rhamnose-3-sulfate(1→, and →4)α-D-Xylose-2-sulfate(1→4)α-L-Rhamnose-3-sulfate(→. The ulvan showed cytotoxic activities against five human cancer cell lines, including human hepatocellular carcinoma, human breast cancer, human cervical cancer, human colorectal adenocarcinoma and human undifferentiated thyroid carcinomas.Keywords: Cytotoxic activitystructureultrasound-assisted extractionUlva lactucaUlvan Disclosure statementNo potential conflict of interest was reported by the author(s).Additional informationFundingThis research is funded by the Ministry of Science and Technology of Vietnam under project number NDT.89.JPN/20.","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"29 4","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134954556","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}

引用次数: 0

Chemoselectivity of 3,3'-dithiobis(sulfosuccinimylpropionate)-based 3-mercaptopropionylation of amine-linked aminomonosaccharides 以3,3'-二硫代丙酸磺基琥珀酰丙酸为基础的胺链氨基单糖3-巯基丙酸化反应的化学选择性

4区化学

Journal of Carbohydrate Chemistry Pub Date : 2023-11-10 DOI: 10.1080/07328303.2023.2280513

Yikuan Qi, Chunjun Qin, Shengyong Zhu, Jian Yin

{"title":"Chemoselectivity of 3,3'-dithiobis(sulfosuccinimylpropionate)-based 3-mercaptopropionylation of amine-linked aminomonosaccharides","authors":"Yikuan Qi, Chunjun Qin, Shengyong Zhu, Jian Yin","doi":"10.1080/07328303.2023.2280513","DOIUrl":"https://doi.org/10.1080/07328303.2023.2280513","url":null,"abstract":"AbstractMany polysaccharides on the surface of bacteria contain free amino groups, limiting the application of amine-based linker in these glycans. Herein, we investigated the chemoselectivity of N-acylation during the dithiobis(sulfosuccinimidylpropionate)-based 3-mercaptopropionylation of amine-linked aminomonosaccharides. Interestingly, for the 2-, 3-, and 4-aminoglucosides and 4-aminogalactoside, the 3-mercaptopropionyl group was selectively installed onto the amine of the linker. The chemoselectivity for the introduction of the thiol moiety was poor with the 2- and 3-aminogalactosides and 2- and 3-aminomannosides. In the meanwhile, the Fukui function was used to further quantify the nucleophilicity of amino groups. These results will serve well for the preparation of conjugation-ready aminoglycans.Keywords: Amino linkeraminosuagrchemoselectivity3,3'-dithiobis(sulfosuccinimidylpropionate)thiol linker Supplemental materialComputational data and NMR spectra of synthetic compounds. This material is available free of charge via the Internet https://www.tandfonline.com/toc/lcar20/current.Disclosure statementNo potential conflict of interest was reported by the author(s).Additional informationFundingThis work was supported by the [National Natural Science Foundation of China] under Grant [number 22077052, 22277042], the [National Key R&D Program of China] under Grant [number 2020YFA0908304].","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":" 10","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135141491","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}

引用次数: 0

A comprehensive study of intravenous iron-carbohydrate nanomedicines: From synthesis methodology to physicochemical and pharmaceutical characterization 静脉注射铁碳水化合物纳米药物的综合研究:从合成方法到物理化学和药物表征

4区化学

Journal of Carbohydrate Chemistry Pub Date : 2023-11-01 DOI: 10.1080/07328303.2023.2272892

Ozra Tabasi, Mahdi Roohi Razlighi, Cavus Falamaki

{"title":"A comprehensive study of intravenous iron-carbohydrate nanomedicines: From synthesis methodology to physicochemical and pharmaceutical characterization","authors":"Ozra Tabasi, Mahdi Roohi Razlighi, Cavus Falamaki","doi":"10.1080/07328303.2023.2272892","DOIUrl":"https://doi.org/10.1080/07328303.2023.2272892","url":null,"abstract":"AbstractAdministration of intravenous iron is pivotal in the management of iron-deficiency anemia patients. In the past, parenteral iron was administrated as a ferric hydroxide complex that caused severe toxic reactions. The introduction of compounds containing iron in a core surrounded by a carbohydrate shell has circumvented this problem. Intravenous iron complexes, such as iron sucrose and iron carboxymaltose, consist of a polynuclear Fe (III)-oxyhydroxide/oxide core that is coated with a specific carbohydrate molecule. The carbohydrate shell stabilizes the insoluble iron core particles in colloidal suspension form and slows down the release of iron. Moreover, the carbohydrate shell chemistry differences influence the stability of the complex and iron release rate. In particular, this paper discusses the preparation method, physicochemical properties, and characteristics of iron sucrose, ferric derisomaltose, iron carboxymaltose, and ferumoxytol. These products differ in their physicochemical and clinical properties such as molecular weight distribution, particle size, zeta potential, free, and labile iron content, stability and release of iron in serum, and maximum tolerated dose. The first-generation of intravenous iron formulations were replaced with new intravenous iron dextran–free formulations, due to an elevated risk of anaphylactic reactions. Comparatively, the third-generation intravenous iron formulations, such as ferric derisomaltose, iron carboxymaltose, and ferumoxytol, allow higher doses of iron due to high complex stability and safety than the second generation formulations like iron sucrose.Keywords: Characterizationintravenous ironiron deficiencyiron formulationssynthesis Disclosure statementNo potential conflict of interest was reported by the author(s).Additional informationFundingNone.","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"201 2","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135325707","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}

引用次数: 0