title: The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates.
abstract: The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani-Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following this strategy, non-natural C-glycosyl type glycoconjugates, which can be utilised as building blocks for the composition of larger molecular constructions, are available by a very short synthetic approach.
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Katharina
authors.initials: K
authors.lastname: Gallas
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Gerit
authors.initials: G
authors.lastname: Pototschnig
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Florian
authors.initials: F
authors.lastname: Adanitsch
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Arnold E
authors.initials: AE
authors.lastname: Stütz
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Tanja M
authors.initials: TM
authors.lastname: Wrodnigg