The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates.
The Amadori rearrangement was introduced as a key step for the conjugation of carbohydrate moieties with suitable amines such as aliphatic amines and amino acid derivatives. The rearrangement products were further transformed into the corresponding 1-N,2-O cyclic carbamates employing triphosgene to obtain anomerically stable glycoconjugates. The reaction conditions were probed on a model substrate, 3,5-di-O-benzyl-alpha,beta-d-glucofuranose and further applied to d-glycero-d-gulo-heptose, which gave 'd-gluco-conjugates' in the alpha-anomeric form exclusively in high isolated yields.
Wrodnigg
Tanja M
TM
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria. t.wrodnigg@tugraz.at
Kartusch
Christiane
C
Illaszewicz
Carina
C
D006001:Glycoconjugates / Q000138:chemical synthesis*
D006001:Glycoconjugates