Approaches to Pyranuronic β-Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers

Viktória Goldschmidt Gőz, István Pintér, Veronika Harmat, András Perczel

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Pyranuronic β-sugar amino acids (β-SAAs) are biocompatible and tuneable building blocks of foldamers and chimera-peptides. The scalable and economical total synthesis of two building blocks is described here. These C-4 epimers, Fmoc-GlcAPU(Me)-OH (7) and Fmoc-GalAPU(Me)-OH (8), which are suitable for solid phase peptide synthesis, were prepared via a common oxime intermediate 16. The new synthesis uses nine consecutive steps, starting from methyl α-d-glucopyranoside (6). The synthesis is fine-tuned, optimized, and ready for large-scale and cost-efficient production.

Original languageEnglish
Pages (from-to)355-361
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number3
DOIs
Publication statusPublished - Jan 23 2018

    Fingerprint

Keywords

  • Amino acids
  • Carbohydrates
  • Foldamers
  • Oximes
  • Peptidomimetics
  • Sugar amino acids

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this