The condensation reaction of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine with glycine ethyl ester hydrochloride

Author: Lika Mebonia
Keywords: The condensation reaction of N-(4-carboxyphenyl)-2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosylamine with glycine ethyl ester hydrochloride
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A n n o t a t i o n Lika Mebonia The condensation reaction of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine with glycine ethyl ester hydrochloride Department of Chemistry, Iv. Javakhishvili Tbilisi State University Ilia Chavchavadze Ave. 3 In recent years, N-glycosides have gained great interest and practical importance in the field of chemistry, biochemistry and medicine. N-glycosides and their derivatives are used as central nervous system mediators, stimulants, also against pests in agriculture. Some synthetic N-glycosides exhibit potential antimetabolic, antiviral, and antitumor activity. The synthesis of new types of derivatives of N-glycosides and the study of their biological activity are still a promising research direction of carbohydrate chemistry. The goal of our work was to synthesize of derivatives of N-(4-carboxyphenyl)-β-D-glucopyranosylamine. N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine has been synthesized from D-glucose and 4-aminobenzoic acid by refluxing in 96% ethanol in the presence of a glacial acetic acid catalyst and by the further acetilation of synthesized N-(4-carboxyphenyl)-β-D-glucopyranosylamine. By condensation of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine with L-glycine ethyl ester hydrochloride in the presence of N,N'-dicyclohexylcarbodiimide and triethylamine at 0C temperature, the N-[4-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)]aminobenzoyl-L-glycine ethyl ester heve been obtained for the first time. The structures of obtainedcompounds were establishedbyphysical-chemicalmethods ofanalysis.

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