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

Published March 04, 2018 21:26

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

Eur. J. Org. Chem. 2018, 355

Ejoc201701612 Toc 0001 M

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