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The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
Cornelia Hojnik1, Anne Müller2, Tobias-Elias Gloe2
1Institute of Organic Chemistry Graz University of Technology Stremayrgasse 9 8010 Graz Austria.
Abstract:
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.
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