Ramanand Das , Rahul Haldar , Irshad Ahmad Zargar , S.K. Bappa , Taraknath Kundu , Debaraj Mukherjee
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A brief account of the application of glycosyl halide as glycosyl radical precursor towards glycosylation through visible light catalysis
Glycosylation is potentially one of the most important reactions in glycochemistry, where precise control over the anomeric selectivity is crucial for synthesizing biologically relevant glycoconjugates. Over the last two decades, the advent of visible light chemistry for the generation of glycosyl radicals and its application in the synthesis of glycosides has revolutionized the impact on the stereoselectivity of glycosylation. The visible light-driven radical-based reactions offer exceptional functional group tolerance, operate under mild reaction conditions, and have emerged as a powerful tool for synthesizing potent glycosyl compounds, which include aryl/alkyl glycosides, 2-deoxy sugar, glycosylamino acid, glycosylpeptides, and other glyco-conjugates. In this review article, a brief account of the evolution of glycosyl radical chemistry, with a focus on the visible light-mediated activation of glycosyl halides and its transformative impact on glycoside synthesis, has been discussed.
期刊介绍:
Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects.
Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence.
Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".