Synthesis (5): 763-769  
DOI: 10.1055/s-0029-1218635
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Assisted Synthesis of Fluorescein-Labelled GalNAcα1-O-Ser/Thr (Tn) Glycopeptides as Immunological Probes

Dong Jun Leea,b, Paul W. R. Harrisa,b, Renata Kowalczyka,b, P. Rod Dunbara,b, Margaret A. Brimble*a,b
a Department of Chemistry, University of Auckland, 23 Symonds St, Auckland 1142, New Zealand
b Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand
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Further Information

Publication History

Received 13 October 2009
Publication Date:
08 January 2010 (online)


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.