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

Goldschmidt Gőz, Viktória and Pintér, István and Harmat, Veronika and Perczel, András (2018) Approaches to Pyranuronic β-Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018 (3). pp. 355-361. ISSN 1434-193X

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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.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Dóra K. Menyhárd
Date Deposited: 30 Jan 2019 09:19
Last Modified: 30 Jan 2019 09:19
URI: http://real.mtak.hu/id/eprint/90727

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