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2 article(s) from Knight, Stefan D

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

Femke Beiroth,
Tomas Koudelka,
Thorsten Overath,
Stefan D. Knight,
Andreas Tholey and
Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

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Graphical Abstract

Figure 1: Principle of photoaffinity labeling of proteins with diazirine derivatives. Photolabile ligands are...

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Figure 2: FimH crystal structure (pdb code 1KLF) with docked p-nitrophenyl α-D-mannopyranoside (1, pNPMan). F...

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Figure 3: Based on the structure of the known FimH ligands 1 and 2, three photolabile α-D-mannosides, 3–5, we...

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Figure 4: Connolly representation of photolabile α-D-mannoside 3 in the closed gate (A, PDB code 1UWF) and op...

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Scheme 1: Synthesis of photolabile α-D-mannosides 3 and 4. a) H₂, Pd-C, methanol, rt, 6 h, 94%; b) HATU, DIPE...

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Figure 5: ESIMS spectra of peptide M2 before (A) and after photoreaction (B) with mannoside 3.

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Figure 6: Intact protein ESIMS spectra of FimH_tr labeling with diazirine derivative 3 with (A) 50% acetonitri...

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Full Research Paper

Published 24 Jul 2018

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En route to photoaffinity labeling of the bacterial lectin FimH

Thisbe K. Lindhorst,
Michaela Märten,
Andreas Fuchs and
Stefan D. Knight

Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91

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Figure 1: The photoaffinity technique allows the identification of ligand binding sites of a receptor protein...

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Figure 2: a) Three known photolabile α-D-mannosides that differ in the nature of the photoactive functional g...

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Scheme 1: Synthesis of photoactive glycoamino acids 11 and 12. i) Fmoc-Asp-OtBu (for 7), Fmoc-Asp(OtBu)-OH (f...

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Scheme 2: Photo-crosslinking experiments with the model peptide angiotensin II and the photoactive mannosides ...

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Figure 3: Affino dot–blot with FimH_tr and photoactive mannosides applied to nitrocellulose disks. It was irra...

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Figure 4: MS/MS spectra of angiotensin II (a) and of angiotensin II, photo-crosslinked with diazirine 2 (b), ...

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Full Research Paper

Published 26 Aug 2010

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