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Information × Registration Number 0208U010122, 0106U003188 , R & D reports Title The obtaining of preparations with potential immunomodulating activity on a basis of muramylpeptides and triterpenoids popup.stage_title Head Chirva Vasily Yakovlevich, Registration Date 08-01-2009 Organization National Taurida V. Vernadsky University popup.description2 The synthetic scheme for obtaining of isomeric donor - acceptor pairs, which was intended for the synthesis of repeating unit of bacterial peptidoglycane by means of intramolecular glycosylation was developed. The conditions of the intramolecular glycoside synthesis, with using of the synthesized compounds were determined. As a result of intramolecular glycosylation reaction, a compound having beta-(1->4)-glycoside bond was obtained, which was structurally analogous to a bacterial peptidoglycane fragment. A variety of N-acylated derivatives of D-glucosamine were synthesized, which were intended for production of muramic acid and its analogues, through the utilization of intramolecular 3-O-alkylation method. The conditions for realization of intramolecular alkylation in the synthesized compounds had been determined and an array of derivatives of muramic acid and its analogues was obtained via newly developed method. The new glycosyl donor with nonparticipating N-protecting group of lactam type had beensynthesized. The stereoselectivity of glycoside synthesis by means of this glycosyl donor was studied and it was ascertained that such donor could be used for stereoselective synthesis of 1,2-cis-glycosidated derivatives of normuramic acid. The individual triterpene glycosides were isolated out of various organs of Dizygotheca elegantissima, Cussonia paniculata, Eleutherococcus senticosus, Kalopanax septemlobus var. typicum, and K. septemlobus var. maximiwiczii and complete chemical structures of these compounds were ascertained with using of chemical hydrolytic methods and one- and two dimensional NMR-spectroscopy methods. Several isolated glycosides are new chemical compounds not described in literature to date. The results of this work could be used for the synthesis of biologically active derivatives of muramic acid and its analogues, including difficultly accessible 1,2-cis-glycosidated muramyl peptides and highly active glycopeptides which are structurally analogous to the repeating unit of bacterial cell wall peptidoglycane. The results of studying of conditions and stereochemistry of intramolecular nucleophilic substitution and glycosylation with using of the new glycosyl donor with nonparticipating N-protecting group are of theoretical interest and can be utilized in carbohydrate chemistry, in particular for development of new methods for production of derivatives of muramic acid and its analogues. It is shown, that the triterpene glycosides from leaves of Cussonia paniculata are very promising for development of molluscicidal drugs, which can be used for prevention of helminthiasis (schistosomiasis) spreading by molluscs. Fungicidal and hemolytic activity was also revealed for monodesmosidic triterpene glycosides. Product Description popup.authors popup.nrat_date 2020-04-02 Close