Amino Acid Derivatives, V [1]: Synthesis and Antiviral Evaluation of α-Amino Acid Esters Bearing an α-d -Mannofuranoside Side Chain |
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Authors: | Omar M Ali and Adel A-H Abdel-Rahman |
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Institution: | (1) Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt;(2) Department of Botany, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt |
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Abstract: | d-Mannose was treated with dry acetone in the presence of conc. H2SO4 to afford 2,3:5,6-di-O-isopropylidene-α-d-mannofuranoside. Treating the latter with ethyl chloroacetate gave carboethoxymethyl 2,3:5,6-di-O-isopropylidene-α-d-mannofuranoside, which was hydrolyzed with N2H4 · H2O to afford the acid hydrazide derivative. Treating of the acid hydrazide with acylated amino acides, via the azide-coupling method afforded the corresponding O-glycopeptides. Reaction of the glycopeptide methyl esters with N2H4 · H2O afforded the corresponding hydrazides, which were coupled with the amino acid methyl esters to afford the dipeptides. Deprotection
was carried out by using 70% AcOH. The prepared O-glycopeptides were tested for antiviral activity against hepatitis B virus and showed moderate activities. |
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