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Synthesis 2010(5): 763-769
DOI: 10.1055/s-0029-1218635
DOI: 10.1055/s-0029-1218635
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Microwave-Assisted Synthesis of Fluorescein-Labelled GalNAcα1-O-Ser/Thr (Tn) Glycopeptides as Immunological Probes
Further Information
Received
13 October 2009
Publication Date:
08 January 2010 (online)
Publication History
Publication Date:
08 January 2010 (online)
Abstract
Fluorescently labelled glycopeptides containing GalNAcα1-O-Ser/Thr residues provide valuable immunological probes for the development of cancer vaccines. The microwave-assisted automated Fmoc solid-phase synthesis of a series of 5(6)-carboxyfluorescein-labelled GalNAcα1-O-Ser/Thr peptides is described. Lys(Dde)-Gly-Wang polystyrene resin was elongated using Fmoc SPPS with incorporation of several GalNAcα1-O-Ser/Thr residues. Deprotection of the Lys(Dde) then allowed attachment of the 5(6)-carboxyfluorescein label. The synthetic methodology described is flexible and suitably robust enabling the incorporation of three contiguous GalNAcα1-O-Ser residues into the peptide chain.
Key words
carbohydrates - glycopeptides - GalNAcα1-O-Ser/Thr amino acids - glycosylations - solid-phase peptide synthesis
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