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Synthesis 2004(4): 525-542
DOI: 10.1055/s-2004-815962
DOI: 10.1055/s-2004-815962
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthetic Tumor-Associated Glycopeptide Antigens from the Tandem Repeat Sequence of the Epithelial Mucin MUC4
Further Information
Received
8 October 2003
Publication Date:
10 February 2004 (online)
Publication History
Publication Date:
10 February 2004 (online)
Abstract
In cancer research, the development of vaccines against tumor-associated antigens is of particular interest. Epithelial cells express mucin type glycoproteins, which are extensively O-glycosylated. In case of cancer, the expression of these mucins is increased, and their carbohydrate side chains show an aberrant glycosylation pattern. A set of single and double glycosylated hexadecapeptides representing the tandem repeat sequence of the epithelial mucin MUC4 carrying different tumor-associated carbohydrate antigens was prepared by sequential solid-phase glycopeptide synthesis. The crucial glycosyl amino acid building blocks containing the TN, T, sialyl-TN and (2,6)-sialyl-T antigens were synthesized according to a biomimetic strategy by stepwise extension of the saccharide side chain of a Fmoc-protected galactosamine threonine tert-butyl ester precursor.
Key words
glycopeptides - glycosylations - mucin MUC4 - sialyl-T antigen - solid-phase synthesis
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