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Solid‐Phase Synthesis of a Sialyl‐Tn‐Glycoundecapeptide of the MUC1 Repeating Unit
Author(s) -
Liebe Beate,
Kunz Horst
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800511
Subject(s) - chemistry , glycopeptide , peptide , solid phase synthesis , muc1 , disaccharide , peptide synthesis , stereochemistry , antigen , threonine , combinatorial chemistry , biochemistry , phosphorylation , immunology , mucin , serine , biology , antibiotics
Abstract The synthesis of glycopeptides carrying tumour‐associated antigens is of interest for cancer diagnosis and treatment. Here, a very efficient route lo disaccharide threonine building block 8 is presented which allows the introduction of the sialyl‐Tn antigen into a peptide. The syntheses of the undecapeptide and the sialyl‐Tn‐containing glycoundecapeptide, which are a part of the repeating unit of MUC1, were performed by solid‐phase synthesis with an allylic anchor cleavable under neutral conditions. After detachment from the resin, the peptide and the glycopeptide arc completely deprotected giving the target compounds 13 and 15 , respectively.