Approaches to Pyranuronic [beta]-Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers

Pyranuronic [beta]-sugar amino acids ([beta]-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 s...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2018-01, Vol.2018 (3), p.355
Main Authors: Goldschmidt Gz, Viktória, Pinter, István, Harmat, Veronika, Perczel, András
Format: Article
Language:English
Subjects:
Amino acids
Biocompatibility
Peptides
Synthesis
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Pyranuronic [beta]-sugar amino acids ([beta]-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 [alpha]-d-glucopyranoside (6). The synthesis is fine-tuned, optimized, and ready for large-scale and cost-efficient production.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701612