Synthesis of Amino-Bridged Oligosaccharide Mimetics

Synthesis of amino-bridged oligosaccharides using reductive amination opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required amino-functionalized units, reduction of azide precursors was advantageous, and generation of the novel oligosaccharides was achieved by subsequent reductive amination. The target saccharide structures feature a bridging nitrogen atom. inserted between two non-anomeric positions as well as including one anomeric position.