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.
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