Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis |
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Authors: | B Lüning T Norberg J Tejbrant |
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Institution: | (1) Department of Organic Chemistry, University of Stockholm, S-106 91 Stockholm, Sweden;(2) Organic Synthesis Department, BioCarb AB, S-223 70 Lund, Sweden |
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Abstract: | N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carryingO-glycosidically - or -linked peracetylated -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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Keywords: | glycopeptide synthesis |
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