The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Cornelia Hojnik, Anne Mueller, Tobias Gloe, Thisbe Lindhorst*, Tanja Wrodnigg*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The Amadori rearrangement was investigated for the synthesis of C-glycosyl-type neoglycoconjugates. Various amines including diamines, amino-functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non-natural C-glycosyl-type glycoconjugates of the d-gluco and d-manno series. 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.
Original languageEnglish
Pages (from-to)4328-4337
JournalEuropean Journal of Organic Chemistry
Issue number25
Publication statusPublished - 2016

Fields of Expertise

  • Human- & Biotechnology

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