Glyco-SAMs as glycocalyx mimetics:: Synthesis of L-fucose- and D-mannose-terminated building blocks

In the course of a project on the supramolecular functions of the glycocalyx present on eukaryotic cell surfaces, it has been our goal to prepare spacer glycosides and cluster glycosides that are suitable for the formation of self-assembled monolayers (SAMs) on gold. We have selected amino-functionalized D-mannose and L-fucose derivatives for peptide coupling to thio-functionalised alkane and alkane-oligoethylene glycol spacers such as 12 and 15. Thus, a variety of thiospacered glycosides (16-19) and cluster glycosides (23, 24, 26, 28, and 29) were synthesized, which can be assembled on gold wafers to serve as glycocalyx mimetics. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).