title: The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations.
abstract: The Amadori rearrangement was investigated for the synthesis ofC-glycosyl-type neoglycoconjugates. Various amines including diamines, amino-functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non-naturalC-glycosyl-type glycoconjugates of the d-glucoand d-mannoseries. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.
authors.affiliation: Institute of Organic Chemistry Graz University of Technology Stremayrgasse 9 8010 Graz Austria.
authors.forename: Cornelia
authors.initials: C
authors.lastname: Hojnik
authors.affiliation: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 24118 Kiel Germany.
authors.forename: Anne
authors.initials: A
authors.lastname: Müller
authors.affiliation: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 24118 Kiel Germany.
authors.forename: Tobias-Elias
authors.initials: TE
authors.lastname: Gloe
authors.affiliation: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 24118 Kiel Germany.
authors.forename: Thisbe K
authors.identifier: 0000-0001-6788-4224
authors.initials: TK
authors.lastname: Lindhorst
authors.affiliation: Institute of Organic Chemistry Graz University of Technology Stremayrgasse 9 8010 Graz Austria.
authors.forename: Tanja M
authors.identifier: 0000-0002-7644-5431
authors.initials: TM
authors.lastname: Wrodnigg
keywords: Carbohydrates; Glycoconjugates; Glycopeptides; Rearrangement; Synthetic methods