Synthesis of Peptide and Glycopeptide Partial Structures of the Homophilic Recognition Domain of Epithelial Cadherin

Tanja Reipen; Horst Kunz

doi:10.1055/s-2003-42429

PAPER

Synthesis of Peptide and Glycopeptide Partial Structures of the Homophilic Recognition Domain of Epithelial Cadherin

Tanja Reipen, Horst Kunz*
Institut für Organische Chemie der Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3924786; e-Mail: hokunz@uni-mainz.de;

Abstract

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Abstract

Peptide and glycopeptide sequences of the homophilic recognition site of epithelial cadherin (E-cadherin) were synthesized by solid-phase technique based on acid-sensitive Wang anchor according to Fmoc strategy. Fmoc serine building blocks with T_N-, T-, (2-6)-sialyl T-antigen and β-N-acetylglucosamine side chains were prepared for the construction of E-cadherin glycopeptides. The T- and (2-6)-sialylT-serine derivatives have been obtained by chemical glycosylations of the T_N-antigen serine derivative carrying Fmoc/tert-butyl ester protecting group combination. According to NOESY and ROESY NMR experiments, E-cadherin(glyco)peptides not acylated at the N-terminus prefer turn-type conformations in water.

Key words

peptides - glycopeptides - solid-phase synthesis - glycosylation - oligosaccharides

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