{"title":"Carbohydrate Chemistry","authors":"A. Rauter, T. Lindhorst, Y. Queneau","doi":"10.1039/9781788013864","DOIUrl":"https://doi.org/10.1039/9781788013864","url":null,"abstract":"","PeriodicalId":89334,"journal":{"name":"Carbohydrate chemistry","volume":"75 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82877254","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Functionalized CARB Pharmacophore (FCP) approach to thio and unsaturated carbohydrate scaffolds with potential anticancer activity","authors":"Z. Witczak, R. Bielski, T. Popławski","doi":"10.1039/9781788013864-00130","DOIUrl":"https://doi.org/10.1039/9781788013864-00130","url":null,"abstract":"This brief review discusses some new developments in the functionalized carb pharmacophore (FCP) concept introduced by us in 2014. While the examples concentrate mainly on biological data of selected newly designed carbohydrate molecules, the chemical syntheses are also included. This review also summarizes new developments in the stereoselective synthesis of 1,4-S-thiodisaccharides and 4-S-thiosaccharides, from levoglucosenone (LG) and a preliminary evaluation of their biological activity. New methodologies utilizing a saturated analog of levoglucosenone, dihydrolevoglucosenone (DHLG), in the synthesis of derivative enones bearing heterocyclic and aromatic moieties at the exocyclic position are also discussed. All exocyclic enones were prepared in good yields by straightforward direct aldol condensation of heterocyclic and aromatic aldehydes with dihydrolevoglucosenone under base conditions. When o-hydroxybenzaldehydes were used as substrates, the original condensation was followed by cyclization forming the domino product, a carbohydrate-fused chromanone system. Additionally, when o-hydroxyacetophenones were used, the base catalysed condensation furnished spiro-chromanones in excellent yield. The stereoselectivities of all reactions are discussed and plausible reaction mechanisms are proposed for the formation of chromanone and spiro-chromanone.","PeriodicalId":89334,"journal":{"name":"Carbohydrate chemistry","volume":"169 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77935310","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Fang Liu, Haipeng Liu, M. Sollogoub, Yongming Zhang
{"title":"Recent advances on glycosphingolipid GM3","authors":"Fang Liu, Haipeng Liu, M. Sollogoub, Yongming Zhang","doi":"10.1039/9781788013864-00230","DOIUrl":"https://doi.org/10.1039/9781788013864-00230","url":null,"abstract":"Ganglioside GM3 has a strong impact on the occurrence and development of human cancer. GM3 is not only overexpressed in several types of cancer but also inhibits tumor cell growth through anti-angiogenesis or motility. In particular, the effect of GM3 on EGFR tyrosine kinase signaling is essential for cancer. GM3 analogs showed better tumor-suppressive activity than GM3. GM3 is also associated with diabetes, regulating the content of GM3 can regulate the mechanism of insulin signaling and improve insulin resistance, which could provide powerful help for the development and application of GM3 and its analogs in the prevention and treatment of type II diabetes. GM3, especially its specifically modified analogs, would become the most promising target molecule for cancer and diabetes treatment.","PeriodicalId":89334,"journal":{"name":"Carbohydrate chemistry","volume":"44 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91190818","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Oxidative deamination of amino sugars: recent advances","authors":"Vikram A. Sarpe, D. Crich","doi":"10.1039/9781788013864-00001","DOIUrl":"https://doi.org/10.1039/9781788013864-00001","url":null,"abstract":"An overview of the oxidative deamination of N-acetylneuraminic acid derivatives (Neu5Ac) leading to the formation of ketodeoxynonulosonic acid (KDN), its stereoisomers and glycosides is presented. A brief historical introduction to the deamination is given, followed by a description of recent advances in reaction conditions, which have allowed application of the process to Neu5Ac thioglycosides, and that have enabled the range of nucleophiles incorporated in the course of the reaction to be extended beyond the original acetate and azide. Recent advances resulting in derivatization of the Neu55Ac 4-position concomitant with replacement of the acetamido group, via the presumed intermediacy of a vinyl diazonium ion, are then described. The literature on the mechanism of the deamination reaction is next considered leading to the presentation of an overall mechanistic framework that accounts for all observations to date. Finally, the application of the deamination reaction to complex Neu5Ac-based oligosaccharides and other aminosugars is presented. settling on the latter as the optimal reagent for further studies. Subsequent reports focused on the N → O migration of the acyl group to form a diazo intermediate, which eliminated nitrogen under thermal conditions giving rise to the corresponding esters. The deamination reaction was studied from multiple angles to ascertain the influence of the alkyl and acyl groups, solvent, and temperature, eventually leading White to propose a mechanism accounting for the formation of various products.","PeriodicalId":89334,"journal":{"name":"Carbohydrate chemistry","volume":"58 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84609167","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Bioorthogonal chemical reporter methodology for visualization, isolation and analysis of glycoconjugates.","authors":"Geert-Jan Boons","doi":"10.1039/9781849730891-00152","DOIUrl":"10.1039/9781849730891-00152","url":null,"abstract":"<p><p>The recent development of metabolic oligosaccharide engineering combined with bioorthogonal reactions is providing unique opportunities to detect, image, and isolate glycoconjugates of living cells, tissues, and model organisms. In this methodology, exogenously-supplied non-natural sugars are fed to cells and employed by the biosynthetic machinery for the biosynthesis of neoglycoconjugates. In this way, reactive functional groups such as ketones, azides, and thiols have been incorporated into sialic acid, galactosamine, glucosamine, and fucose moieties of glycoconjugates. A range of bioorthogonal reactions have been described that functionalize the chemical 'tags' for imaging, isolation, and drug delivery.</p>","PeriodicalId":89334,"journal":{"name":"Carbohydrate chemistry","volume":"36 ","pages":"152-167"},"PeriodicalIF":0.0,"publicationDate":"2010-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3142093/pdf/nihms-245235.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"30029691","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Disaccharides as building blocks for novel glycomacrocycles","authors":"Patrycja Sokołowska, S. Jarosz","doi":"10.1039/9781839164538-00442","DOIUrl":"https://doi.org/10.1039/9781839164538-00442","url":null,"abstract":"","PeriodicalId":89334,"journal":{"name":"Carbohydrate chemistry","volume":"48 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"1900-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88634332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}