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Synthesis 2003(16): 2487-2502
DOI: 10.1055/s-2003-42429
DOI: 10.1055/s-2003-42429
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Peptide and Glycopeptide Partial Structures of the Homophilic Recognition Domain of Epithelial Cadherin
Further Information
Received
15 July 2003
Publication Date:
14 October 2003 (online)
Publication History
Publication Date:
14 October 2003 (online)
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 TN-, 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 TN-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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