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

Authors
  • Lüning, B
  • Norberg, T
  • Tejbrant, J
Type
Published Article
Journal
Glycoconjugate journal
Publication Date
Jan 01, 1989
Volume
6
Issue
1
Pages
5–19
Identifiers
PMID: 2535477
Source
Medline
License
Unknown

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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