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3 article(s) from Wittmann, Valentin

Cyclopropene derivatives of aminosugars for metabolic glycoengineering

Jessica Hassenrück and
Valentin Wittmann

Beilstein J. Org. Chem. 2019, 15, 584–601, doi:10.3762/bjoc.15.54

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Figure 1: Cyclopropene-modified mannosamine, glucosamine and galactosamine derivatives employed for MGE.

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Figure 2: A) Reaction of ManNCyc and ManNCp, respectively, with Tz-PEG-OH to determine second-order rate cons...

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Scheme 1: MGE with cyclopropene-modified mannosamines. Cells were grown with sugar for 48 hours and then incu...

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Figure 3: HEK 293T cells were grown with 100 μM Ac₄ManNCyc, Ac₄ManNCp, Ac₄ManNCyoc or DMSO only (negative con...

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Scheme 2: Synthesis of Ac₄ManNCp(H₂) and Ac₄ManNCyc(H₂) and the corresponding DMB-labeled sialic acids. C/A =...

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Scheme 3: Synthesis of Ac₄ManNCyoc(H₂) and the corresponding DMB-labeled sialic acid.

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Scheme 4: Synthesis of Ac₄GlcNCp and Ac₄GalNCp.

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Figure 4: HEK 293T cells were grown with 100 μM Ac₄ManNCp, Ac₄GlcNCp, Ac₄GalNCp or DMSO only (negative contro...

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Figure 5: HEK 293T cells were grown with 100 μM Ac₄GlcNCp, Ac₄GalNCp or DMSO only (negative control) for 48 h...

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Figure 6: HEK 293T cells were grown with 50 μM (A) or 100 μM (B) Ac₄GlcNCp, Ac₄GlcNCyoc or DMSO only (negativ...

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Figure 7: Western blot analysis of soluble glycoproteins. HEK 293T cells were grown for 48 h with 100 μM Ac₄M...

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Scheme 5: Synthesis of Ac₄GlcNCp(H₂) and Ac₄GlcNCyoc(H₂).

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Published 04 Mar 2019

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Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

Anne-Katrin Späte,
Verena F. Schart,
Julia Häfner,
Andrea Niederwieser,
Thomas U. Mayer and
Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

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Scheme 1: Principle of MOE with Ac₄GlcNCyoc (1) and subsequent ligation by a DAinv reaction: The chemically m...

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Figure 1: Hexosamine derivatives with cyclopropene tags. Cyoc = (2-methylcycloprop-2-en-1-yl)methoxycarbonyl,...

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Scheme 2: Synthesis of the cyclopropene-modified hexosamine derivatives 1 and 2.

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Scheme 3: Labeling strategy for metabolically incorporated monosaccharides.

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Figure 2: Labeling of metabolically engineered cell-surface glycoconjugates. HEK 293T cells were grown for 48...

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Figure 3: Western blot analysis of soluble glycoproteins. HeLa S3 cells were grown for 48 h with 100 µM cyclo...

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Published 22 Sep 2014

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High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

Henning S. G. Beckmann,
Heiko M. Möller and
Valentin Wittmann

Beilstein J. Org. Chem. 2012, 8, 819–826, doi:10.3762/bjoc.8.91

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Figure 1: Amines used for the synthesis of glycoclusters.

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Scheme 1: Synthesis of glycocluster B5 with isolation of the intermediate diazide 2.

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Scheme 2: Deacetylation of glycoconjugates B1–B6. (a) NaOMe, MeOH.

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Scheme 3: Formation of side-product 5 during the synthesis of 4.

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Figure 2: Dose-response curves for the inhibition of binding of HRP-labeled WGA to covalently immobilized Glc...

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Figure 3: Molecular model of divalent ligand C4 with its two chitobiose moieties occupying two adjacent bindi...

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Published 01 Jun 2012

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