Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2006, Issue 23, Pages 5357-5366Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200600612
Keywords
carbohydrates; glycoclusters; amphiphilic glycoconjugates; glycolipid mimetics
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Glycolipids are involved in many cellular recognition processes, so there is a need for their synthesis as well as for the design and preparation of glycolipid mimetics. In addition to the application of glycolipid mimetics in a glycobiological context, they are also of interest in many other fields of research, due to their amphiphilic characters. Our goal was to elaborate a series of known orthogonally functionalized glycomimetics and cluster glycosides into glycomimetics of a glycolipid type, so monosaccharide building blocks such as 3, glycodendrons such as 19, and branched cluster glycosides of the type 24 were ligated with lipophilic molecules by peptide coupling, this conjugation providing a new class of complex amphiphilic glycoconjugates with high molecular diversity.
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