The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

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...

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Detalles Bibliográficos
Autores principales: Hojnik, Cornelia, Müller, Anne, Gloe, Tobias‐Elias, Lindhorst, Thisbe K., Wrodnigg, Tanja M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5094532/
https://www.ncbi.nlm.nih.gov/pubmed/27840588
http://dx.doi.org/10.1002/ejoc.201600458
Descripción
Sumario: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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