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1 article(s) from Stamer, Insa

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

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Graphical Abstract

Scheme 1: The Amadori rearrangement of aldoses with amines leads to C-glycosyl-type glycoconjugates, namely 1...

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Figure 1: The bacterial lectin FimH is known to bind α-D-mannosides such as methyl α-D-mannoside 1 (MeMan) wi...

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Scheme 2: Synthesis of D-glycero-D-galacto/D-talo-heptopyranose 8a and 8b: a) O₃, NaOAc, Me₂S, CH₂Cl₂/MeOH, −...

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Scheme 3: Amadori rearrangement of heptoaldose 8 with propargylamine and aniline to yield C-glycosyl-type D-m...

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Figure 2: Cartoon illustrating ligand binding by the bacterial lectin FimH. Complexation of D-manno-configure...

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Figure 3: Partial charge coloured Connolly descriptions [28,29] (negative partial charges coloured in red, positive ...

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Figure 4: Comparison of mannosides as complexed within the CRD of FimH (PDB 1KLF). A: MeMan (1); B: Amadori p...

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Published 30 Jun 2015

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