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Glycosylated foldamers: synthesis of carbohydrate-modified β3hSer and incorporation into β-peptides

✍ Scribed by Anna S. Norgren; Thomas Norberg; Per I. Arvidsson

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
214 KB
Volume
13
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

Fmoc‐protected β^3^hserine (β^3^hSer) was prepared and O‐linked to suitably protected N‐acetylgalactosamine (GalNAc) and N‐acetylglucosamine (GlcNAc) derivatives. Glycosylation of β^3^hSer was made by two independent routes: either by direct glycosyl linkage to the β^3^hSer, or linkage to natural L‐Ser and then utilizing the carbohydrate moiety as a protecting group in an Arndt–Eistert homologation. Both procedures gave the novel glycosylated β^3^‐amino acids Fmoc‐β^3^hSer(α‐D‐GalNAc(Ac)~3~)‐OH (1a), its β‐anomer (1b), and Fmoc‐β^3^hSer(β‐D‐GlcNAc(Ac)~3~)‐OH (2), which were utilized in the solid‐phase peptide synthesis of four glycosylated dipeptides (3a–d) and two heptapeptides (4a–b). The preparation of β‐amino acids bearing common post‐translational modifiers represents an important step towards functionalized foldamers with broad applications in biomedical research. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.

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