Glycosylated foldamers: synthesis of carbohydrate-modified beta3hSer and incorporation into beta-peptides.
Fmoc-protected beta(3)hserine (beta(3)hSer) was prepared and O-linked to suitably protected N-acetylgalactosamine (GalNAc) and N-acetylglucosamine (GlcNAc) derivatives. Glycosylation of beta(3)hSer was made by two independent routes: either by direct glycosyl linkage to the beta(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 beta(3)-amino acids Fmoc-beta(3)hSer(alpha-D-GalNAc(Ac)(3))-OH (1a), its beta-anomer (1b), and Fmoc-beta(3)hSer(beta-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 beta-amino acids bearing common post-translational modifiers represents an important step towards functionalized foldamers with broad applications in biomedical research.
Norgren
Anna S
AS
Department of Biochemistry & Organic Chemistry, Uppsala University, S-75123 Uppsala, Sweden.
Norberg
Thomas
T
Arvidsson
Per I
PI
D002241:Carbohydrates / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D011487:Protein Conformation; D017510:Protein Folding; D012694:Serine / Q000737:chemistry*
D002241:Carbohydrates; D010455:Peptides; D012694:Serine