SummaryThe Amadori rearrangement was employed for the synthesis of C-glycosyl-type D-mannoside analogues, namely 1-propargylamino- and 1-phenylamino-1-deoxy-α-D-manno-heptopyranose. They were investigated as ligands of type 1-fimbriated E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori rearrangement products have a limited activity as inhibitors of bacterial adhesion because the β-C-glycosidically linked aglycone considerably hampers complexation within the carbohydrate binding site of the type 1-fimbrial lectin FimH.

The cover picture shows the Amadori rearrangement, which allows the conjugation of carbohydrate moieties to diverse amino components, such as amino acids, lysine‐containing peptides, complex amino‐functionalized glycosides, as well as di‐ and triamines in one step without protecting‐group manipulations. The linkage through a C‐glycosidic‐type conjugation, which is not sensitive towards enzymatic or chemical hydrolysis in a physiological environment, leads to versatile building blocks for different applications, in particular for biological investigations. Details are discussed in the article by T. K. Lindhorst, T. M. Wrodnigg et al. on http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600458/abstract.

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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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