2-Benzofuranyl C-glycosides were synthesized in good to excellent yields by one-pot cascade reaction of terminal sugar alkynes and substituted 2-iodophenols. The products have wide structural diversity and potential biological activity. This new synthetic method is general, mild, and efficient. Thirty-seven examples have been given. The structurally diverse terminal sugar alkynes included pyranosides, furanosides, and acyclic sugars with sensitive and bulky protecting groups. The substituted 2-iodophenols contained electron-donating, electron-withdrawing, and electron-neutral substituents. The mechanism for the formation of the products has been proposed.
{"title":"Efficient synthesis of 2-benzofuranyl C-glycosides by one-pot cascade reaction of sugar alkynes and substituted 2-iodophenols","authors":"Zhaoxin Cao , Xiang Zhou , Fuyi Zhang , Yufen Zhao","doi":"10.1080/07328303.2023.2280538","DOIUrl":"10.1080/07328303.2023.2280538","url":null,"abstract":"<div><div>2-Benzofuranyl <em>C</em>-glycosides were synthesized in good to excellent yields by one-pot cascade reaction of terminal sugar alkynes and substituted 2-iodophenols. The products have wide structural diversity and potential biological activity. This new synthetic method is general, mild, and efficient. Thirty-seven examples have been given. The structurally diverse terminal sugar alkynes included pyranosides, furanosides, and acyclic sugars with sensitive and bulky protecting groups. The substituted 2-iodophenols contained electron-donating, electron-withdrawing, and electron-neutral substituents. The mechanism for the formation of the products has been proposed.</div></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"42 4","pages":"Pages 135-157"},"PeriodicalIF":1.2,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138584863","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 : 2023-07-03eCollection Date: 2023-01-01DOI: 10.3897/zookeys.1168.97845
Zhongyan Zhou, Lianmeng Wei
Two new species of Phaonia are described: Phaoniaagitata Zhou & Wei, sp. nov. and Phaonianujiangensis Zhou & Wei, sp. nov., which were collected from Guizhou and Yunnan provinces of southwestern China and are assigned to the boleticola-group. A key to the species of this group is provided. The type specimens are deposited in the Wei Lianmeng Model Worker Innovation Studio, Anshun, Guizhou, China (WLMWISAGC).
{"title":"Two new species of the <i>Phaoniaboleticola</i>-group (Diptera, Muscidae, Phaoniinae) from China.","authors":"Zhongyan Zhou, Lianmeng Wei","doi":"10.3897/zookeys.1168.97845","DOIUrl":"10.3897/zookeys.1168.97845","url":null,"abstract":"<p><p>Two new species of <i>Phaonia</i> are described: <i>Phaoniaagitata</i> Zhou & Wei, <b>sp. nov.</b> and <i>Phaonianujiangensis</i> Zhou & Wei, <b>sp. nov.</b>, which were collected from Guizhou and Yunnan provinces of southwestern China and are assigned to the <i>boleticola</i>-group. A key to the species of this group is provided. The type specimens are deposited in the Wei Lianmeng Model Worker Innovation Studio, Anshun, Guizhou, China (WLMWISAGC).</p>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"12 1","pages":"219-229"},"PeriodicalIF":1.3,"publicationDate":"2023-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10848857/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81753757","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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.
{"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.
摘要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。关键词:细胞毒活性;结构;超声辅助提取;本研究由越南科技部资助，项目编号为NDT.89.JPN/20。
{"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.
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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。
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