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Synthesis of Amino‐Bridged Oligosaccharide Mimetics
Author(s) -
Neumann Janna,
Thiem Joachim
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901106
Subject(s) - chemistry , reductive amination , amination , azide , anomer , combinatorial chemistry , stereochemistry , amino acid , oligosaccharide , nitrogen atom , organic chemistry , alkyl , biochemistry , catalysis
Abstract 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.