Glucuronic acid derivatives as branching units for the synthesis of glycopeptide mimetics.
Natural glycopeptides and glycoproteins exhibit a large structural diversity, which can be mimicked by synthetic glycopeptide derivatives to assist the investigation of biological functions and structure-activity relationships. Here, dendronized saccharides were synthesized to provide glycosyl amino acids, equipped with a branching element for the preparation of branched glycopeptide mimetics. An optimized Staudinger-type reaction served as key reaction en route to the complex glycopeptide 14, in which three mannose moieties were connected to the branched glucuronyl scaffold.
Röckendorf
Niels
N
Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 3, 24098 Kiel, Germany.
Lindhorst
Thisbe K
TK
D000596:Amino Acids / Q000737:chemistry; D005965:Glucuronates / Q000138:chemical synthesis / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D015394:Molecular Structure
D000596:Amino Acids; D005965:Glucuronates; D006020:Glycopeptides