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Synthesis 2010(5): 828-836  
DOI: 10.1055/s-0029-1218611
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Glyco-SAMs by ‘Dual Click’: Thiourea-Bridged Glyco-OEG Azides for Cycloaddition on Surfaces

Carsten Graboscha, Mike Kleinertb, Thisbe K. Lindhorst*a
a Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn Platz 3, 24098 Kiel, Germany
Fax: +49(431)8807410; e-Mail: tklind@oc.uni-kiel.de;
b Department of Chemistry, University of Bergen, Allégaten 41, 5007 Bergen, Norway
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Publication History

Received 5 October 2009
Publication Date:
22 December 2009 (online)

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Abstract

A series of NCS-functionalized sugars were synthesized and used in a thiourea-bridging reaction with aminohexa(ethylene glycol) azide [H2N(EG)6N3], a bifunctional oligo(ethylene glycol) derivative, which can be used as key intermediate for the fabrication of biorepulsive glyco-SAMs by a ‘dual click’ approach. Glyco-SAMs can serve as defined glycocalyx models for the study of carbohydrate-protein interactions. The copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of the obtained glyco-OEG azides was exemplified, which can be used to modify preformed monolayers ‘on SAM’.

Key words

carbohydrates - self-assembled monolayers - ‘click’ chemistry - thiourea-bridging