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Updated: Aug 15, 2026

Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
Published on: November 2, 2011
Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis
B Lüning1, T Norberg, J Tejbrant
1Department of Organic Chemistry, University of Stockholm, Sweden.
Abstract:
N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carrying O-glycosidically alpha- or beta-linked peracetylated beta-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 of N-fluorenylmethyloxycarbonyl amino-acid phenacyl esters. Removal of the phenacyl esters with zinc gave the target free acids.
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