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Amino Acid Derivatives, IV [1]: Synthesis and Antiviral Evaluation of New α-Amino Acid Esters Bearing Methyl β-d-Ribofuranoside Side Chain

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Summary.

Methyl 2,3-O-isopropylidene-β-d-ribofuranoside was synthesized and oxidized with HIO4 to afford the corresponding carboxylic acid. The latter was coupled with the appropriate acylated amino acids in the presence of HOBt and DDC as coupling reagents to give the corresponding amides. The methyl acetate derivative was hydrolyzed with 2 N KOH/MeOH to the corresponding carboxylic acid, which was coupled with l-glycine methyl ester to furnish the amide. Deprotection was carried out with 70% AcOH at reflux temperature. The prepared glycopeptides were tested for antiviral activity against Herpes Simplex virus type-1 (HSV-1) and hepatitis-A virus (HAV). The plaque reduction infectivity assay was used to determine virus count reduction as a result of treatment with tested compounds.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt

    Ibrahim A. I. Ali

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

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

Authors
  1. Ibrahim A. I. Ali
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  2. Omar M. Ali
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  3. Adel A.-H. Abdel-Rahman
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Correspondence to Adel A.-H. Abdel-Rahman.

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Ali, I., Ali, O. & Abdel-Rahman, AH. Amino Acid Derivatives, IV [1]: Synthesis and Antiviral Evaluation of New α-Amino Acid Esters Bearing Methyl β-d-Ribofuranoside Side Chain. Monatsh. Chem. 138, 909–915 (2007). https://doi.org/10.1007/s00706-007-0643-0

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  • DOI: https://doi.org/10.1007/s00706-007-0643-0

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