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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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Summary.

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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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt

    Omar M. Ali & Adel A.-H. Abdel-Rahman

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  1. Omar M. Ali
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  2. Adel A.-H. Abdel-Rahman
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Correspondence to Adel A.-H. Abdel-Rahman.

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Ali, O., Abdel-Rahman, AH. Amino Acid Derivatives, V [1]: Synthesis and Antiviral Evaluation of α-Amino Acid Esters Bearing an α-d-Mannofuranoside Side Chain. Monatsh. Chem. 139, 53–60 (2008). https://doi.org/10.1007/s00706-007-0734-y

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  • DOI: https://doi.org/10.1007/s00706-007-0734-y

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