Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

• Tobias-Elias Gloe,
• Insa Stamer,
• Cornelia Hojnik,
• Tanja M. Wrodnigg and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 1096–1104, doi:10.3762/bjoc.11.123

• ]. However, we could show that the Amadori rearrangement, when applied to selected aldoses as starting materials, is a high yielding and efficient synthetic approach towards C-glycosyl-type glycoconjugates. For example, when aldoheptoses are employed as starting material for the Amadori rearrangement, the

• efficient and versatile approach towards D-manno-configured C-glycosyl-type glycoconjugates. In our study, we have employed two different amines in the Amadori rearrangement with 8, propargylamine and aniline. Under typical conditions for this reaction [2] 1-progargylamino-1-deoxy-D-manno-heptulose 9 and 1

• carbohydrate binding site that is interacting mainly with the 2-OH group of the sugar ring. When the standard FimH ligand MeMan (1) is compared with the D-manno-configured C-glycosyl-type glycoconjugates 9 and 10, emerging from Amadori rearrangement of the corresponding heptopyranose 8, the axial methoxy

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

• Katharina Gallas,
• Gerit Pototschnig,
• Florian Adanitsch,
• Arnold E. Stütz and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

• been synthesised. Following this strategy, non-natural C-glycosyl type glycoconjugates, which can be utilised as building blocks for the composition of larger molecular constructions, are available by a very short synthetic approach. Keywords: Amadori rearrangement; C-glycosyl type glycoconjugates

• adopt an equatorial position in the 5C2 pyranoid conformation, which is a strong driving force providing excellent preparative yields [25]. In general, this reaction leads to non-natural C-glycosyl type glycoconjugates, which are of particular interest for biological investigation because of their

• -natural C-glycosyl type glycoconjugates in the D-manno, D-galacto as well as GlcNAc series starting from the respective aldoheptoses and suitable amino components. Aldoheptoses were synthesised by C-elongation of the corresponding hexoses and subsequent reductive hydrolysis following the Kiliani–Fischer