Anomeric modification of carbohydrates using the Mitsunobu reaction

• Julia Hain,
• Patrick Rollin,
• Werner Klaffke and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

• conditions requires a sufficiently acidic NH nucleophile. A particularly illustrative procedure was disclosed by van Boom’s group, who used N-nosyl-activated amino-acid esters for anomeric modification of sugars in order to produce substrates for a novel route to Amadori rearrangement products [86]. The same

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

• Graz, Stremayrgasse 9, A-8010 Graz, Austria 10.3762/bjoc.11.123 Abstract The 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. Keywords: Amadori rearrangement; bacterial adhesion; C-mannosides; docking studies; FimH ligands; Introduction The Amadori rearrangement (AR) is the reaction in which aldohexoses react with suitable amines under acidic catalysis to 1-amino-1-deoxyketohexoses

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

• Katharina Gallas Gerit Pototschnig Florian Adanitsch Arnold E. Stutz Tanja M. Wrodnigg Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria 10.3762/bjoc.8.185 Abstract The Amadori rearrangement was investigated as a potential method for the

• 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

• -group manipulations should be kept to a minimum. Considering these aspects, we were interested in probing the Amadori rearrangement as a conjugation method for the synthesis of glycoconjugates. The Amadori rearrangement (AR) allows the formation of 1-aminodeoxyketoses 2 and 3 from the respective aldose