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Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis

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Abstract

N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carryingO-glycosidically α- or β-linked peracetylated β-d-Galp-(1–3)-d-GalNAcp carbohydrate chains, were prepared. These derivatives are intended for use in solid phase glycopeptide synthesis. Suitably protected mono- and disaccharide thioglycosides were used as carbohydrate intermediates. These were activated by treatment with bromine to give the glycosyl bromides, which were then used in silver triflate-promoted glycosidations ofN-fluorenylmethyloxycarbonyl amino-acid phenacyl esters. Removal of the phenacyl esters with zinc gave the target free acids.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Stockholm, S-106 91, Stockholm, Sweden

    B Lüning & J Tejbrant

  2. Organic Synthesis Department, BioCarb AB, S-223 70, Lund, Sweden

    T Norberg

Authors
  1. B Lüning
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  2. T Norberg
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  3. J Tejbrant
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Lüning, B., Norberg, T. & Tejbrant, J. Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis. Glycoconjugate J 6, 5–19 (1989). https://doi.org/10.1007/BF01047886

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  • DOI: https://doi.org/10.1007/BF01047886

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