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Synthesis 2009(3): 488-494  
DOI: 10.1055/s-0028-1083302
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

On-Resin Click-Glycoconjugation of Peptoids

Anna S. Norgrena, Carsten Budkeb, Zsuzsa Majerc, Carolin Heggemanna, Thomas Koopb, Norbert Sewald*a
a Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, PO Box 10 01 31, 33501 Bielefeld, Germany
e-Mail: norbert.sewald@uni-bielefeld.de;
b Department of Chemistry, Physical Chemistry, Bielefeld University, 33501 Bielefeld, Germany
c Institute of Chemistry, Eötvös University, 1117 Budapest, Hungary
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Publication History

Received 4 June 2008
Publication Date:
09 January 2009 (online)

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Abstract

Peptoids are unnatural peptide-like oligomers having the side-chain attached to the glycine nitrogen. In order to investigate how such oligomers are affected upon glycoconjugation, a series of glycosylated peptoids has been synthesized. The conjugation between glycosyl residue and peptoid was achieved by azide + alkyne [3+2] cycloaddition (click reaction). The glycosylated peptoids were obtained by either stepwise assembly from sarcosine and glycosylated monomers or global on-resin click glycoconjugation. CD spectroscopic studies were performed on both unglycosylated and glycosylated peptoids with varying chain-length, revealing length and substituent dependences. Additionally, three peptoids were tested for antifreeze activity.

Key words

glycoconjugation - peptoids - click chemistry - triazoles - CD - antifreeze testing