Functionalization of oligosaccharide mimetics and multimerization using squaric diester-mediated coupling.
Functionalized carbohydrate-centered glycoclusters formed the starting material for the synthesis of tagged oligosaccharide and glycoconjugate mimetics, which were obtained by thiourea-bridging, peptide coupling and in particular squaric diester-mediated coupling. The latter method could also be utilized to provide new multivalent glycoconjugates, which were tested for their anti-adhesive properties in an ELISA with Escherichia coli bacteria.
Sperling
Oliver
O
Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 4, 24098 Kiel, Germany.
Dubber
Michael
M
Lindhorst
Thisbe K
TK
D001422:Bacterial Adhesion; D002240:Carbohydrate Sequence; D003503:Cyclobutanes / Q000737:chemistry*; D004797:Enzyme-Linked Immunosorbent Assay; D004926:Escherichia coli / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry; D006001:Glycoconjugates / Q000737:chemistry; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry
D003503:Cyclobutanes; D005456:Fluorescent Dyes; D006001:Glycoconjugates; D009844:Oligosaccharides; D013890:Thiourea; C030042:squaric acid