Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids

Laiqiang Ying, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.

Original languageEnglish (US)
Pages (from-to)367-375
Number of pages9
JournalCarbohydrate Research
Volume339
Issue number2
DOIs
StatePublished - Jan 22 2004

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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