Pub Date : 2023-03-24DOI: 10.1080/07328303.2023.2242927
Jiayu Dong , Katsunari Hiroki , Mizuki Tobito , Keisuke Yoshida , Ai Tanabe , Taiki Shindo , Megu Gunji , Qintong Li , Teruaki Hasegawa
Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides were prepared via a three-step synthetic route, involving (1) NaIO4 oxidation of commercially available nata de coco, (2) reductive amination of the product using propargylamine, and (3) Cu+-catalysed alkyne-azide cycloaddition using azide-functionalised Lewis X trisaccharides. The resultant bacterial cellulose-based hydrogels were assembled in aqueous media containing Ca2+ or Na+, demonstrating ion-mediated interactions among Lewis X trisaccharides. Furthermore, reference experiments using bacterial cellulose-based hydrogels carrying N-acetyl-lactosaminides and those carrying N-acetyl-D-glucosaminides revealed that the two non-reducing terminals (i.e., β-galactoside and α-fucoside of Lewis X trisaccharide) substantially contribute to their interactions.
以细菌纤维素为基础，通过三步合成路线制备了携带Lewis X三糖的水凝胶，包括：(1)NaIO4氧化市售可可脂，(2)丙胺还原胺化产物，(3)Cu+催化叠氮化Lewis X三糖的炔-叠氮化环加成。所得的细菌纤维素基水凝胶在含有Ca2+或Na+的水介质中组装，证明了Lewis X三糖之间离子介导的相互作用。此外，使用携带n-乙酰-乳糖胺和携带n-乙酰- d -氨基葡萄糖的细菌纤维素水凝胶进行的参考实验表明，两个非还原末端（即Lewis X三糖的β-半乳糖苷和α-聚焦蛋白）在很大程度上促进了它们的相互作用。
{"title":"Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides as a system for monitoring carbohydrate–carbohydrate interactions with the naked eye","authors":"Jiayu Dong , Katsunari Hiroki , Mizuki Tobito , Keisuke Yoshida , Ai Tanabe , Taiki Shindo , Megu Gunji , Qintong Li , Teruaki Hasegawa","doi":"10.1080/07328303.2023.2242927","DOIUrl":"10.1080/07328303.2023.2242927","url":null,"abstract":"<div><div>Bacterial cellulose-based hydrogels carrying Lewis X trisaccharides were prepared via a three-step synthetic route, involving (1) NaIO<sub>4</sub> oxidation of commercially available <em>nata de coco</em>, (2) reductive amination of the product using propargylamine, and (3) Cu<sup>+</sup>-catalysed alkyne-azide cycloaddition using azide-functionalised Lewis X trisaccharides. The resultant bacterial cellulose-based hydrogels were assembled in aqueous media containing Ca<sup>2+</sup> or Na<sup>+</sup>, demonstrating ion-mediated interactions among Lewis X trisaccharides. Furthermore, reference experiments using bacterial cellulose-based hydrogels carrying <em>N</em>-acetyl-lactosaminides and those carrying <em>N</em>-acetyl-D-glucosaminides revealed that the two non-reducing terminals (i.e., β-galactoside and α-fucoside of Lewis X trisaccharide) substantially contribute to their interactions.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 13","pages":"Pages 40-58"},"PeriodicalIF":1.2,"publicationDate":"2023-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44791093","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}
Many 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.
{"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":"10.1080/07328303.2023.2280513","url":null,"abstract":"<div><div>Many 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 <em>N</em>-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.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 13","pages":"Pages 59-91"},"PeriodicalIF":1.2,"publicationDate":"2023-03-24","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}
Pub Date : 2023-03-24DOI: 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
An 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.
采用超声辅助提取的方法，从绿海藻中提取一种紫檀素。采用响应面法对提取条件进行优化。最佳提取条件为提取温度84.75℃，提取时间30.51 min，料液比60.51 mL/g，得率为22.5%。该化合物由三个双糖组成：→4)-β- d -葡萄糖醛酸（1→4）α- l -鼠李糖-3-硫酸盐（1→，→4）α- l -伊杜醛酸（1→4）α- d -木糖-2-硫酸盐（1→4）α- l -鼠李糖-3-硫酸盐（1→，→4）α- d -木糖-2-硫酸盐（1→4）α- l -鼠李糖-3-硫酸盐（→）。对人肝癌、人乳腺癌、人宫颈癌、人结直肠腺癌和人未分化甲状腺癌等5种人类癌细胞系均有细胞毒活性。
{"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":"10.1080/07328303.2023.2280560","url":null,"abstract":"<div><div>An ulvan was extracted from green seaweed <em>Ulva lactuca</em> 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.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 13","pages":"Pages 92-111"},"PeriodicalIF":1.2,"publicationDate":"2023-03-24","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}
Carbohydrate-binding proteins known as “Lectins” play a crucial role in host-pathogen interactions. Most of the viral surface proteins have lectin activity. In fact, they make the first line of communication with the host cells. Recent reports indicating the haemagglutination property and structural evidences of coronaviral protein bound with Sialic acid (Sia) draw our attention to exploring the presence of lectins in the Betacoronavirus genus from reference genomes. We have considered the seventeen reference genomes of different species and subspecies under the Betacoronavirus genus to identify lectin fold/domain(s) types. We have employed three strategies for characterizing lectin fold/domain(s). The strategies include the sequence-based search against the conserved domain database (CDD) and profile HMMER and Structure-based search against Protein Data Bank (PDB) and unified platform of lectins UniLectin3D database. Interestingly, both the identified proteins, namely Hemagglutinin-esterase (HE) and Spike (S) protein, were localized on viral membranes and played a pivotal role in host-pathogen interactions. These protein structures are fabricated by most pliable β-strands forming varied architectures and topologies, such as β-sandwich, jelly-roll fold, β-barrel, β-prism, β-trefoil, β-propeller and β-hairpins. The identified lectin fold/domain(s) were compared with the characterized ones and were docked with Sia using HADDOCK, and the binding affinity was calculated using the PRODIGY server. Molecular docking studies reveal that all the identified lectin fold/domains agree with the Canyon hypothesis. Furthermore, it could be observed that coronaviruses are constantly evolving by shedding their extra baggage. The latter variants were found to have only the lectin domain but not the esterase domain.
{"title":"Betacoronaviral lectins: Identification through a genomic search—A structural and evolutionary biology perspective","authors":"Pavan K. Madasu , Arpita Maity , Dhabaleswar Patra , Thyageshwar Chandran","doi":"10.1080/07328303.2023.2285970","DOIUrl":"10.1080/07328303.2023.2285970","url":null,"abstract":"<div><div>Carbohydrate-binding proteins known as “Lectins” play a crucial role in host-pathogen interactions. Most of the viral surface proteins have lectin activity. In fact, they make the first line of communication with the host cells. Recent reports indicating the haemagglutination property and structural evidences of coronaviral protein bound with Sialic acid (Sia) draw our attention to exploring the presence of lectins in the Betacoronavirus genus from reference genomes. We have considered the seventeen reference genomes of different species and subspecies under the Betacoronavirus genus to identify lectin fold/domain(s) types. We have employed three strategies for characterizing lectin fold/domain(s). The strategies include the sequence-based search against the conserved domain database (CDD) and profile HMMER and Structure-based search against Protein Data Bank (PDB) and unified platform of lectins UniLectin3D database. Interestingly, both the identified proteins, namely Hemagglutinin-esterase (HE) and Spike (S) protein, were localized on viral membranes and played a pivotal role in host-pathogen interactions. These protein structures are fabricated by most pliable β-strands forming varied architectures and topologies, such as β-sandwich, jelly-roll fold, β-barrel, β-prism, β-trefoil, β-propeller and β-hairpins. The identified lectin fold/domain(s) were compared with the characterized ones and were docked with Sia using HADDOCK, and the binding affinity was calculated using the PRODIGY server. Molecular docking studies reveal that all the identified lectin fold/domains agree with the Canyon hypothesis. Furthermore, it could be observed that coronaviruses are constantly evolving by shedding their extra baggage. The latter variants were found to have only the lectin domain but not the esterase domain.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 13","pages":"Pages 112-134"},"PeriodicalIF":1.2,"publicationDate":"2023-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143292443","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}
Administration 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.
{"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":"10.1080/07328303.2023.2272892","url":null,"abstract":"<div><div>Administration 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.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 13","pages":"Pages 1-39"},"PeriodicalIF":1.2,"publicationDate":"2023-03-24","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}
Pub Date : 2022-01-01DOI: 10.1080/07328303.2023.2189473
Anjali Sharma , Smritilekha Bera , Dhananjoy Mondal
Carbohydrates are the most abundant natural products and a major component on the cell surface of living beings. They are useful building blocks of various natural products and organic synthesis due to their presence of multiple chiral centers and hydroxy groups. The recent outbreak of COVID-19 and other life-threatening viral infections necessitates the development of potent antiviral drugs. In this review, we focused on the synthesis of antiviral drugs to treat influenza, HIV, herpes, hepatitis, and other diseases, from different monosaccharides such as D-glucose, D-mannose, D-xylose, N-acetyl-D-glucosamine, D-gluconolactone, etc., such as anti-influenza drugs remdesivir, Tamiflu, zanamivir, and so on.
Download : Download high-res image (247KB)
Download : Download full-size image
碳水化合物是最丰富的天然产物，是生物细胞表面的主要成分。由于它们的多个手性中心和羟基的存在，它们是各种天然产物和有机合成的有用基石。最近爆发的COVID-19和其他危及生命的病毒感染要求开发强效抗病毒药物。本文综述了以d -葡萄糖、d -甘露糖、d -木糖、n -乙酰- d -葡萄糖胺、d -葡萄糖酸内酯等不同单糖为原料，如抗流感药物瑞德西韦、达菲、扎那米韦等，合成治疗流感、HIV、疱疹、肝炎等疾病的抗病毒药物。下载:下载高分辨率图片(247KB)下载:下载全尺寸图片
{"title":"Advances in the synthesis of antiviral agents from carbohydrate-derived chiral pools","authors":"Anjali Sharma , Smritilekha Bera , Dhananjoy Mondal","doi":"10.1080/07328303.2023.2189473","DOIUrl":"10.1080/07328303.2023.2189473","url":null,"abstract":"<div><p>Carbohydrates are the most abundant natural products and a major component on the cell surface of living beings. They are useful building blocks of various natural products and organic synthesis due to their presence of multiple chiral centers and hydroxy groups. The recent outbreak of COVID-19 and other life-threatening viral infections necessitates the development of potent antiviral drugs. In this review, we focused on the synthesis of antiviral drugs to treat influenza, HIV, herpes, hepatitis, and other diseases, from different monosaccharides such as D-glucose, D-mannose, D-xylose, <em>N</em>-acetyl-D-glucosamine, D-gluconolactone, etc., such as anti-influenza drugs remdesivir, Tamiflu, zanamivir, and so on.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (247KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 7","pages":"Pages 424-510"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42321811","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}
Pub Date : 2022-01-01DOI: 10.1080/07328303.2022.2039685
Nuha S. Kareem , Shaymaa A. Mohammed , May Jaleel Abed , Asaad H. Aneed , Hayder M. Kamal , N. Idayu Zahid , Karem J. Sabah
A series of new macrocycles based on alkyl glycosides derived from D-glucose and D-galactose was synthesized. The macrocycles were easily obtained by the reaction of dialkynyl derivatives with diazides via copper-catlyzed 1,3-cycloaddition reaction. Simple protecting group strategies were applied to obtain the vicinal dihydroxy derivatives, followed by Williamson etherification with propargyl bromides to get the dialkynyl derivatives. These derivatives were subjected to 1,3-Hüisgen triazole coupling with diazides furnishing the macrocycles in good yields. The 1,3-Hüisgen reaction used to build these macrocycles was investigated thoroughly with respect to reaction time, catalysts, solvents, and temperature for optimum macrocyclisation.
{"title":"New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling","authors":"Nuha S. Kareem , Shaymaa A. Mohammed , May Jaleel Abed , Asaad H. Aneed , Hayder M. Kamal , N. Idayu Zahid , Karem J. Sabah","doi":"10.1080/07328303.2022.2039685","DOIUrl":"10.1080/07328303.2022.2039685","url":null,"abstract":"<div><p>A series of new macrocycles based on alkyl glycosides derived from D-glucose and D-galactose was synthesized. The macrocycles were easily obtained by the reaction of dialkynyl derivatives with diazides via copper-catlyzed 1,3-cycloaddition reaction. Simple protecting group strategies were applied to obtain the vicinal dihydroxy derivatives, followed by Williamson etherification with propargyl bromides to get the dialkynyl derivatives. These derivatives were subjected to 1,3-Hüisgen triazole coupling with diazides furnishing the macrocycles in good yields. The 1,3-Hüisgen reaction used to build these macrocycles was investigated thoroughly with respect to reaction time, catalysts, solvents, and temperature for optimum macrocyclisation.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 1","pages":"Pages 1-17"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44472605","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}
Pub Date : 2022-01-01DOI: 10.1080/07328303.2022.2055049
Hongli Hou , Guangzong Tian , Junjie Fu , Chunjun Qin , Guodong Chen , Xiaopeng Zou , Jing Hu , Jian Yin
The highly stereoselective synthesis of complex carbohydrates containing 1,2-cis-quinovosamine is an on-going challenge. Here, we report a synergistic strategy of merging reagent modulation and acyl remote participation for highly stereoselective construction of 1,2-cis-D-quinovosamine linkages. The strategy is applied to the preparation of natural disaccharide present on the surface of Pseudomonas aeruginosa bacteria. The resulting disaccharide can be covalently bound to microarray surface or carrier via the aminopentyl linker at the reducing end, allowing for exploring its antigenic and immunogenic properties.
高度立体选择性合成含有1,2-顺式-喹诺糖胺的复合碳水化合物是一个持续的挑战。在这里，我们报道了一种融合试剂调制和酰基远程参与的协同策略，用于高度立体选择性的1,2-顺式- d -喹诺胺键的构建。该方法应用于铜绿假单胞菌表面天然双糖的制备。所得到的双糖可以通过还原端的氨基戊基连接物与微阵列表面或载体共价结合，从而可以探索其抗原和免疫原性。
{"title":"Highly stereoselective construction of 1,2-cis-D-quinovosamine glycosides for the synthesis of Pseudomonas aeruginosa O-antigen disaccharide","authors":"Hongli Hou , Guangzong Tian , Junjie Fu , Chunjun Qin , Guodong Chen , Xiaopeng Zou , Jing Hu , Jian Yin","doi":"10.1080/07328303.2022.2055049","DOIUrl":"10.1080/07328303.2022.2055049","url":null,"abstract":"<div><p>The highly stereoselective synthesis of complex carbohydrates containing 1,2-<em>cis</em>-quinovosamine is an on-going challenge. Here, we report a synergistic strategy of merging reagent modulation and acyl remote participation for highly stereoselective construction of 1,2-<em>cis</em>-D-quinovosamine linkages. The strategy is applied to the preparation of natural disaccharide present on the surface of <em>Pseudomonas aeruginosa</em> bacteria. The resulting disaccharide can be covalently bound to microarray surface or carrier via the aminopentyl linker at the reducing end, allowing for exploring its antigenic and immunogenic properties.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 2","pages":"Pages 155-180"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44036718","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}
Pub Date : 2022-01-01DOI: 10.1080/07328303.2022.2063308
Zhongwu Guo
Glycosphingolipids (GSLs) are a subclass of glycolipids made of a glycan and a ceramide that, in turn, is composed of a sphingoid base moiety and a fatty acyl group. GSLs represent the vast majority of glycolipids in eukaryotes, and as an essential component of the cell membrane, they play an important role in many biological and pathological processes. Therefore, they are useful targets for the development of novel diagnostic and therapeutic methods for human diseases. Since sphingosine was first described by J. L. Thudichum in 1884, several hundred GSL species, not including their diverse lipid forms that can further amplify the number of individual GSLs by many folds, have been isolated from natural sources and structurally characterized. This review tries to provide a comprehensive survey of the major GSL species, especially those with distinct glycan structures and modification patterns, and the ceramides with unique modifications of the lipid chains, that have been discovered to date. In particular, this review is focused on GSLs from eukaryotic species. This review has listed 251 GSL glycans with different linkages, 127 glycans with unique modifications, 46 sphingoids, and 43 fatty acyl groups. It should be helpful for scientists who are interested in GSLs, from isolation and structural analyses to chemical and enzymatic syntheses, as well as their biological studies and applications.
鞘糖脂(GSLs)是由糖聚糖和神经酰胺组成的糖脂的一个亚类，而神经酰胺又由鞘基部分和脂肪酰基组成。GSLs代表了真核生物中绝大多数的糖脂，是细胞膜的重要组成部分，在许多生物和病理过程中起着重要作用。因此，它们是开发新的人类疾病诊断和治疗方法的有用靶点。自1884年J. L. Thudichum首次描述鞘氨醇以来，已有数百种GSL从天然来源中分离出来并进行了结构表征，其中不包括它们的多种脂质形式，这些脂质形式可以进一步将GSL的个体数量扩增许多倍。本文综述了迄今为止发现的主要GSL物种，特别是具有独特聚糖结构和修饰模式的GSL物种，以及具有独特脂链修饰的神经酰胺。本文特别对真核生物的gsl进行了综述。本文综述了251种具有不同键的GSL聚糖，127种具有独特修饰的GSL聚糖，46个鞘和43个脂肪酰基。它应该有助于对gsl感兴趣的科学家，从分离和结构分析到化学和酶合成，以及它们的生物学研究和应用。
{"title":"The structural diversity of natural glycosphingolipids (GSLs)","authors":"Zhongwu Guo","doi":"10.1080/07328303.2022.2063308","DOIUrl":"10.1080/07328303.2022.2063308","url":null,"abstract":"<div><p>Glycosphingolipids (GSLs) are a subclass of glycolipids made of a glycan and a ceramide that, in turn, is composed of a sphingoid base moiety and a fatty acyl group. GSLs represent the vast majority of glycolipids in eukaryotes, and as an essential component of the cell membrane, they play an important role in many biological and pathological processes. Therefore, they are useful targets for the development of novel diagnostic and therapeutic methods for human diseases. Since sphingosine was first described by J. L. Thudichum in 1884, several hundred GSL species, not including their diverse lipid forms that can further amplify the number of individual GSLs by many folds, have been isolated from natural sources and structurally characterized. This review tries to provide a comprehensive survey of the major GSL species, especially those with distinct glycan structures and modification patterns, and the ceramides with unique modifications of the lipid chains, that have been discovered to date. In particular, this review is focused on GSLs from eukaryotic species. This review has listed 251 GSL glycans with different linkages, 127 glycans with unique modifications, 46 sphingoids, and 43 fatty acyl groups. It should be helpful for scientists who are interested in GSLs, from isolation and structural analyses to chemical and enzymatic syntheses, as well as their biological studies and applications.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 2","pages":"Pages 63-154"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10427639","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}
Pub Date : 2022-01-01DOI: 10.1080/07328303.2022.2077358
Kendall C. Craig , Zhongwu Guo
A diacyl phosphatidylinositol (PI) derivative with an azide linked to its inositol C4-position was effectively synthesized in 19 steps for the longest linear sequence and in a ca. 1% overall yield from 1,2-distearoyl-sn-glycerol and D-glucose. This compound was designed as a biosynthetic precursor of glycosylphosphatidylinositol (GPI) anchors. Its azide would enable further modification to introduce other molecular tags by a biocompatible click reaction. Therefore, it can be a useful probe for metabolic engineering of cell surface GPI anchors and GPI-anchored proteins.
{"title":"Design and synthesis of 4-azido-phosphatidylinositol as a potential probe for metabolic engineering of glycosylphosphatidylinositol on cells","authors":"Kendall C. Craig , Zhongwu Guo","doi":"10.1080/07328303.2022.2077358","DOIUrl":"10.1080/07328303.2022.2077358","url":null,"abstract":"<div><p>A diacyl phosphatidylinositol (PI) derivative with an azide linked to its inositol C4-position was effectively synthesized in 19 steps for the longest linear sequence and in a <em>ca</em>. 1% overall yield from 1,2-distearoyl-<em>sn</em>-glycerol and D-glucose. This compound was designed as a biosynthetic precursor of glycosylphosphatidylinositol (GPI) anchors. Its azide would enable further modification to introduce other molecular tags by a biocompatible click reaction. Therefore, it can be a useful probe for metabolic engineering of cell surface GPI anchors and GPI-anchored proteins.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (26KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"41 4","pages":"Pages 238-248"},"PeriodicalIF":1.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10474761","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}
扫码关注我们
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号