Sidorova E. Synthesis and modification of glucosaminides

Object of investigation: a- and b-glycosides of N-acetyl-D-glucosamine, synthesis of Kenigs-Knorr, muramoyldipeptide. Aim of investigation: the optimization of the novel way of synthesis of N-acetylglucosamine glycosides as the inters for the synthesis of glycolipids, spacer-arm glucosaminides and glycosides of N-acetylmuramoyl-L-alanyl-D-isoglutamine. Methods of investigation and equipment: organic synthesis, IR, NMR spectroscopy. Theoretical results and their novelty: the conditions of prevailing formation of а- and b-glycosides of N-acetyl-D-glucosamine while glycosilisation of alcohols using 2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-a-D-glucopyranosylchloride under the conditions of Kenigs-Knorr reaction in the presence of the mercury (II) iodide promoter are determined. Under the conditions of investigated reaction the regioselectivity and stereoselectivity of glycosilisation reaction of 4,6-diol derivatives of N-acetyl-D-glucosamine with a-D-glycopyranozilechloride peracetate is discovered. The methods of synthesis of 1,2-cis and 1,2-trans-glucoseaminides based on alcohols of different structure, namely aliphatic, alicyclic, steroid, adamantylalcanols, arylalcanols and w-chloroalcohols are developed. The novel glycoside of muramoyldipeptide, e.g. the methyl ester of b-2-(naphtyl-1)-ethyl-N-acetylmuramoyl-L-alanyl-D-isoglutamine is synthesized and its immunostimulating properties are investigated. Practical results and their novelty: the developed ways of synthesis of diastereomeric glucosaminides having aglycones of different structure can be used for deriving of the novel inters in carbohydrate synthesis: disaccharides, glycolipids, spacer-arm glucoseaminides, glycoconjugates. The synthesized glycosides of N-acetyl-D-glucosamine are the basic substances for carrying out the investigations concerning synthesis and study of the significant group of a- and b-derivatives of muramoyldipeptide and the creation of the novel immunostimulatingagents. Subject and the degree of introduction: publications, reports at the scientific conferences, using the results of work in the scientific and pedagogical practice of establishments of higher education and Scientific Research Institutes of Ukraine. Efficiency of introduction is ensured by the development of the novel way of Kenigs-Knorr synthesis of 1,2-cis- and 1,2-trans-O-glucoseaminides and the determination of conditions of their prevailing formation. Sphere of use: chemistry.