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

Dong Jun Lee; Paul W. R. Harris; Renata Kowalczyk; P. Rod Dunbar; Margaret A. Brimble

doi:10.1055/s-0029-1218635

PAPER

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

Dong Jun Lee^a,b, Paul W. R. Harris^a,b, Renata Kowalczyk^a,b, P. Rod Dunbar^a,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
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Abstract

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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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