Deutsch Intern
THE SEIBEL GROUP: ORGANIC AND BIOLOGICAL CHEMISTRY

2023-2014

David Harris, Marcel Groß, Sebastian Staebler, Regina Ebert, Jürgen Seibel and Anja Katrin Boßerhoff

Modifying the Glycocalyx of Melanoma Cells via Metabolic Glycoengineering Using N-Acetyl-D-glucosamine Analogues

Cells 2024, 13(22), 1831

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Marcel Rühling, Louise Kersting, Fabienne Wagner, Fabian Schumacher, Dominik Wigger, Dominic A. Helmerich, Tom Pfeuffer, Robin Elflein, Christian Kappe, Markus Sauer, Christoph Arenz, Burkhard Kleuser, Thomas Rudel, Martin Fraunholz & Jürgen Seibel

Trifunctional sphingomyelin derivatives enable nanoscale resolution of sphingomyelin turnover in physiological and infection processes via expansion microscopy

Nat. Commun 2024, 15, 7456

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Mingzhen Fan, Patrick Kiefer, Paul Charki, Christian Hedberg, Jürgen Seibel, Julia A. Vorholt and Hubert Hilbi

The Legionella autoinducer LAI-1 is delivered by outer membrane vesicles to promote interbacterial and interkingdom signaling

J. Biol. Chem. 2023, 299(12), 105376

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Christine Sternstein, Theresa-Maria Böhm, Julian Fink, Jessica Meyr, Martin Lüdemann, Melanie Krug, Kirill Kriukov, Cenk O. Gurdap, Erdinc Sezgin, Regina Ebert and Jürgen Seibel

Development of an Effective Functional Lipid Anchor for Membranes (FLAME) for the Bioorthogonal Modification of the Lipid Bilayer of Mesenchymal Stromal Cells

Bioconjugate Chem. 2023, 34, 7, 1221-12331

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Maria Elena Ortiz-Soto, Makarius Baier, Daniela Brenner, Malte Timm and Jürgen Seibel

Single-mutations at the galactose-binding site of enzymes GalK, GalU and LgtC enable the efficient synthesis of UDP-6-azido-6-deoxy-D-galactose and azido-functionalized Gb3 analogs

Glycobiology 2023, cwad045

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Angela Münch, Lorenz Weihrich, Niclas Knoblauch and Prof. Dr. Jürgen Seibel

Employing Click Chemistry to Expand the Scope of the Metal-Free Donor-Acceptor Type Photocatalyst 4CzIPN

Eur. J. Org. Chem. 2023, 26, e202300279

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Daniela Brenner, Nina Geiger, Jan Schlegel, Viktoria Diesendorf, Louise Kersting, Julian Fink, Linda Stelz, Sibylle Schneider-Schaulies, Markus Sauer, Jochen Bodem, Jürgen Seibel

Azido-Ceramides, a Tool to Analyse SARS-CoV-2 Replication and Inhibition—SARS-CoV-2 Is Inhibited by Ceramides

Int. J. Mol. Sci. 2023, 24(8), 7281

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Jürgen Mut, Stephan Altmann, Sabine Reising, Jutta Meißner-Weigl, Marc D. Driessen, Regina Ebert, Jürgen Seibel

SiaNAl can be efficiently incorporated in glycoproteins of human mesenchymal stromal cells by metabolic glycoengineering

ACS Biomater. Sci. Eng. 2023

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Ahmed M. Sayed, Alyaa Hatem Ibrahim, Nasir Tajuddeen, Jürgen Seibel, Jochen Bodem, Nina Geiger, Kathrin Striffler, Gerhard Bringmann, Usama Ramadan Abdelmohsen

Korupensamine A, but not its atropisomer, korupensamine B, inhibits SARS-CoV-2 in vitro by targeting its main protease (Mpro)

Eur. J. Med. Chem. 2023, 251, 115226

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Christine Sternstein, Jan Schlegel, Markus Sauer, Jürgen Seibel

Bioorthogonal azido-S1P works as substrate for S1PR1,

J. Lipid Res. 2023, 64 (1), 100311 

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Nina Geiger, Louise Kersting, Jan Schlegel, Linda Stelz, Sofie Fähr, Viktoria Diesendorf, Valeria Roll, Marie Sostmann, Eva-Maria König, Sebastian Reinhard, Daniela Brenner, Sibylle Schneider-Schaulies, Markus Sauer, Jürgen Seibel and Jochen Bodem

The Acid Ceramidase Is a SARS-CoV-2 Host Factor,

Cells 202211(16), 2532

Die Zellen in der oberen Reihe wurden mit dem Fluoxetin-ähnlichen Molekül AKS466 behandelt und danach mit SARS-CoV-2 infiziert. Die Zellen unten wurden nur infiziert; in ihnen ist deutlich mehr virale RNA nachweisbar (hellere Punkte).

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Sascha Eder, Claudia Hollmann, Putri Mandasari, Pia Wittmann, Fabian Schumacher , Burkhard Kleuser, Julian Fink, Jürgen Seibel, Jürgen Schneider-Schaulies, Christian Stigloher, Niklas Beyersdorf and Sofia Dembski

Synthesis and Characterization of Ceramide-Containing Liposomes as Membrane Models for Different T Cell Subpopulations,

J. Funct. Biomater. 202213(3), 111

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Sibylle Schneider-Schaulies, Fabian Schumacher, Dominik Wigger, Marie Schöl, Trushnal Waghmare, Jan Schlegel, Jürgen Seibel and Burkhard Kleuser

Sphingolipids: Effectors and Achilles Heals in Viral Infections?,

Cells 202110(9), 2175

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Marco R. Rink, Marisa A. P. Baptista, Felix J. Flomm, Thomas Hennig, Adam W. Whisnant, Natalia Wolf, Jürgen Seibel, Lars Dölken, Jens B. Bosse

Concatemeric Broccoli reduces mRNA stability and induces aggregates,

PLoS ONE 2021, 16(8), e0244166

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Jürgen Seibel, Sibylle Schneider-Schaulies and Burkhard Kleuser

Editorial: Sphingolipids in Infection Control,

Front. Cell Dev. Biol. 20219, 697290

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Florian Pinzner, Thorsten Keller, Jürgen Mut, Julian Bechold, Jürgen Seibel and Jürgen Groll

Polyoxazolines with a Vicinally Double-Bioactivated Terminus for Biomacromolecular Affinity Assessment,

Sensors 202121(9), 3153

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Melissa Zimniak, Luisa Kirschner, Helen Hilpert, Nina Geiger, Olga Danov, Heike Oberwinkler, Maria Steinke, Katherina Sewald, Jürgen Seibel and Jochen Bodem

The serotonin reuptake inhibitor Fluoxetine inhibits SARS-CoV-2 in human lung tissue,

Sci. Rep. 2021, 11, 5890

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Stephan Altmann, Jürgen Mut, Natalia Wolf, Jutta Meißner-Weigl, Maximilian Rudert, Franz Jakob, Marcus Gutmann, Tessa Lühmann, Jürgen Seibel and Regina Ebert

Metabolic Glycoengineering in hMSC-TERT as a Model for Skeletal Precursors by Using Modified Azide/Alkyne Monosaccharides,

Int. J. Mol. Sci. 202122(6), 2820

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S. Peters, L. Kaiser, J. Fink, F. Schumacher, V. Perschin, J. Schlegel, M. Sauer, C. Stigloher, B. Kleuser, J. Seibel and A. Schubert-Unkmeir

Click-correlative light and electron microscopy (click-AT-CLEM) for imaging and tracking azido-functionalized sphingolipids in bacteria,

Sci. Rep. 2021, 11, 1-12.

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Julian Fink, Fabian Schumacher, Jan Schlegel, Philipp Stenzel, Dominik Wigger, Markus Sauer, Burkhard Kleuser, and Jürgen Seibel

Azidosphinganine enables metabolic labeling and detection of sphingolipid de novo synthesis,

Org. Biomol. Chem., 2021

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Teresa Wiese, Fabio Dennstädt, Claudia Hollmann, Saskia Stonawski, Catherina Wurst, Julian Fink, Erika Gorte1, Putri Mandasari, Katharina Domschke, Leif Hommers, Bernard Vanhove, Fabian Schumacher10, Burkhard Kleuser, Jürgen Seibel, Jan Rohr, Mathias Buttmann, Andreas Menke, Jürgen Schneider- Schaulies, Niklas Beyersdorf

Inhibition of acid sphingomyelinase increases regulatory T cells in humans

Brain Communications, 2021,, fcab020, https://doi.org/10.1093/braincomms/fcab020

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Ralph Götz, Tobias Kunz, Julian Fink, Franziska Solger, Jan Schlegel, Jürgen Seibel, Vera Kozjak-Pavlovic, Thomas Rudel, Markus Sauer

Nanoscale imaging of bacterial infections by sphingolipid expansion microscopy

Nat Commun 2020, 11, 6173

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Fink J., Seibel J., Avota E. 

Detection of Functionalized Sphingolipid Analogs in Detergent-Resistant Membranes of Immune Cells

In: Bieberich E. (eds) Lipid Rafts. Methods in Molecular Biology, vol 2187. Humana, New York, NY

 

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N. Wolf, L. Kersting, C. Herok, C. Mihm, J. Seibel

High Yielding Water-Soluble Asymmetric Cyanine Dyes for Labeling Applications

J. Org. Chem.. 2020, 85, 9751–9760.

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P.J. Smith, M.E. Ortiz-Soto, C. Roth, W. J. Barnes, J. Seibel, B. R. Urbanowicz, F. Pfrengle

Enzymatic Synthesis of Artificial Polysaccharides

ACS Sustainable Chem. Eng. 2020, 32, 11853–11871.

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K. Rajeeve, N. Vollmuth, S. Janaki-Raman, T. Wulff, M. Schmalhofer, W. Schmitz, A. Baluapuri, C. Huber, J. Fink, F. R. Dejure, E. Wolf, W. Eisenreich, A. Schulze, J. Seibel, T. Rudel

Reprogramming of host glutamine metabolism during Chlamydia trachomatis infection and its key role in peptidoglycan synthesis

Nature Microbiology 2020, 5, 1390–1402.

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ME Ortiz-Soto, JR Porras-Domínguez, ME Rodríguez-Alegría, LA Morales-Moreno, A Díaz-Vilchis, E Rudiño-Piñera, NE Beltrán-Hernandez, HM Rivera, J Seibel, A López Munguía

Implications of the mutation S164A on Bacillus subtilis levansucrase product specificity and insights into protein interactions acting upon levan synthesis

Int. J. Biol. Macromolecules 2020, 161, 898-908.

 

 

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F. Solger, T. C. Kunz, J. Fink, F. Schumacher, K. Paprotka, P. Pfister, F. Hagen, B. Kleuser, J. Seibel, T. Rudel

A role of sphingosine in the intracellular survival of Neisseria gonorrhoeae

Front. Cell. Infect. Microbiol. 2020, 10250, doi.10.3389/fcimb.2020.00215

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Judith Lang, Patrick Bohn, Hilal Bhat, Holger Jastrow, Bernd Walkenfort, Feyza Cansiz, Julian Fink, Michael Bauer, Dominik Olszewski, Ana Ramos-Nascimento, Vikas Duhan, Sarah-Kim Friedrich, Katrin Anne Becker, Adalbert Krawczyk, Michael J. Edwards, Andreas Burchert, Magdalena Huber, Justa Friebus-Kardash, Joachim R. Göthert, Cornelia Hardt, Hans Christian Probst, Fabian Schumacher, Karl Köhrer, Burkhard Kleuser, Eduard B. Babiychuk, Beate Sodeik, Jürgen Seibel, Urs F. Greber, Philipp A. Lang, Erich Gulbins & Karl S. Lang

Acid ceramidase of macrophages traps herpes simplex virus in multivesicular bodies and protects from severe disease

Nat Commun 2020, 11, 1338doi:10.1038/s41467-020-15072-8

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M. E. Ortiz-Soto, S. Reising, A. Schlosser, J. Seibel

Structural and functional role of disulphide bonds and substrate binding residues of the human beta-galactoside alpha-2,3-sialyltransferase 1 (hST3Gal1)

Sci Rep 2019, 9, 17993, doi:10.1038/s41598-019-54384-8

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C. Hollmann, T. Wiese, F. Dennstädt, J. Fink, J. Schneider-Schaulies, N. Beyersdorf

Translational Approaches Targeting Ceramide Generation From Sphingomyelin in T Cells to Modulate Immunity in Humans

Fron. Immunol. 2019https://doi.org/10.3389/fimmu.2019.02363.

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T Wiese, F Dennstaedt, C Hollmann, S Stonawski, C Wurst, J Fink, J Seibel, J Rohr, M Buttmann, A Menke, J Schneider-Schaulies, N Beyersdorf

CD4+ Foxp3+ regulatory T cell-mediated immunomodulation by pharmacological inhibition of the acid sphingomyelinase in humans

EUROPEAN JOURNAL OF IMMUNOLOGY  2019, 49, 283.

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V. Merz,  J. Lenhart,  Y. Vonhausen,  M. E. Ortiz‐Soto,  J. Seibel,  A. Krueger

Nanodiamond with Superior Protein Repulsion and Colloidal Stability in Physiological Media

Small  2019, 15(48):e1901551. doi: 10.1002/smll.201901551.

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G. Beliu, A. Kurz, A. Kuhlemann, L. Behringer-Pliess, N. Wolf, J. Seibel, Zhen-Dan Shi, M. Schnermann, J. B. Grimm, L. D. Lavis, S. Doose, M. Sauer

Bioorthogonal labeling with tetrazine-dyes for super-resolution microscopy

Commun Biol. 2019, 2, 261. doi: 10.1038/s42003-019-0518-z. eCollection 2019.

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M. E. Ortiz-Soto, J.R. Porras-Domínguez, J. Seibel, A. López-munguía

A close look at the structural features and reaction conditions that modulate the synthesis of low and high molecular weight fructans by levansucrases

Carbohydrat Polymers 2019, 219, 130-142.

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C. Possiel, M. E. Ortiz-Soto, J. Ertl, A. Münch, A. Vogel, R. Schmiedel, J. Seibel

Exploring the sequence variability of polymerization-involved residues in the production of levan- and inulin-type fructooligosaccharides with a levansucrase

Scientific Reports 2019, 9, 7720.

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L. Irsheid, T. Wehler, C. Borek, W. Kiefer, R. Brenk, M. E. Ortiz-Soto, J. Seibel, T. Schirmeister

Identification of a potential allosteric site of Golgi α-mannosidase II using computer-aided drug design

PLoS ONE  2019, 14 (5), e0216132.

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J. Ertl, M. E. Ortiz-Soto, T. A. Le, J. Bechold, J. Shan, J. Teßmar, B. Engels, J. Seibel

Tuning the product spectrum of a glycoside hydrolase enzyme by a combination of site‐directed mutagenesis and tyrosine‐specific chemical modification

Chemistry - A European Journal 2019, 25, 6533-6541.

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M. Gutmann, J. Bechold, J. Seibel, L. Meinel, T. Lühmann

Metabolic glycoengineering of cell derived matrices and cell surfaces – a combination of key principles and step-to-step procedures

ACS Biomater. Sci. Eng.  2019, 5 (1), 215–233.

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D. Kaiser, J. M. Winne, M. E. Ortiz-Soto, J. Seibel, T. Anh Le, B. Engels

Mechanistical insights into the bioconjugation
reaction of Triazolinediones with tyrosine

J. Org. Chem. 2018, 83, 10248–10260.

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M. Kraus, C. Grimm, J. Seibel

Reversibility of a Point Mutation Induced Domain Shift: Expanding the Conformational Space of a Sucrose Phosphorylase

Scientific Reports  2018, 8, 10490.

 

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M. E. Ortiz-Soto, J. Ertl, J. Mut, J. Adelmann, T. A. Le, J. Shan, J. Teßmar, A. Schlosser, B. Engels, J. Seibel

Product-oriented chemical surface modification of a levansucrase (SacB) via an ene-type reaction 

Chem. Sci.  2018, 9, 5312-5321.

 

 

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J. Fink, J. Seibel

Click reactions with functional Sphingolipids

Biol. Chem. 2018399(10), 1157-1168.

 

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M. Gutmann, A. Braun, J. Seibel, T. Lühmann

Bioorthogonal modification of cell derived matrices by metabolic glyco-engineering

ACS Biomaterials Science & Engineering 2018, 4, 1300-1306.

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J. Seibel, C. Grimm, J. Bechold

Mit Zucker gegen Bösartiges

Nachrichten aus der Chemie 2018, 66 (1), 30-31.

 


J. Becam, T. Walter, A. Burgert, J. Schlegel, M. Sauer, J. Seibel, A. Schubert-Unkmeir

Antibacterial activity of ceramide and ceramide analogs against pathogenic Neisseria

Scientific Reports 2017, 7, Article number: 17627 (2017)

 

 

 

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M. Kraus, C. Grimm, J. Seibel

Switching enzyme specificity from phosphate to resveratrol glucosylation

Chem. Commun. 2017, 53, 12181 - 12184.


 

C. Possiel, A. Bäuerle, J. Seibel

A novel Chemoenzymatic route to a new class of Sucrose esters

Eur. J. Org. Chem. 2017, 6335–6337.


­­J. Görl, C. Possiel, C. Sotriffer, J. Seibel,

Extending the Scope of GTFR Glucosylation Reactions with Tosylated Substrates for Rare Sugars Synthesis

ChemBioChem 201718, 2012-2015.

 

 


M. Elena Ortiz-Soto, C. Possiel, J. Görl, A. Vogel, R. Schmiedel, J. Seibel

Impaired coordination of nucleophile and increased hydrophobicity in the +1 subsite shift levansucrase activity towards transfructosylation

Glycobiology 201727, 755-765.

 


 

N. Bertleff-Zieschang, J. Bechold, C. Grimm, M. Reutlinger, P. Schneider, G. Schneider, J. Seibel

Exploring the structural space of galectin-1-ligand interaction

ChemBioChem 2017, 18, 1477-1481.

 


T. Walter,  J. Schlegel,  A. Burgert, A. Kurz,  J. Seibel and M. Sauer

Incorporation studies of clickable ceramides in Jurkat cell plasma membranes

Chem. Commun2017, 53, 6836-6839.


 


M. Ortiz-Soto, J. Seibel

Molecular Engineering of Enzymes
Applied Bioengineering: Innovations and Future Directions 2017


Stephan Wawra, Philipp Fesel, Heidi Widmer, Malte Timm, Jürgen Seibel, Lisa Leson, Leona Kesseler, Robin Nostadt, Magdalena Hilbert, Gregor Langen & Alga Zuccaro
The fungal-specific β-glucan-binding lectin FGB1 alters cell-wall composition and suppresses glucan-triggered immunity in plants
Nat. Commun. 2016, 7, 13188.

 


A. Mertsch, S. Letschert, E. Memmel, M. Sauer, J. Seibel
Synthesis and application of water soluble, photoswitchable cyanine dyes for bioorthogonal labeling of cell-surface carbohydrates
Biosciences – Zeitschrift für Naturforschung C 2016, 71, 347–354.

 


J. Seibel
ZNC opens a new chapter focussing on the emerging field of natural and natural-like compounds
Biosciences – Zeitschrift für Naturforschung C 2016, 71, 93

 


M. Ortiz-Soto, J. Seibel
From gene to product: tailor-made oligosaccharides and polysaccharides by enzyme and substrate engineering
Carbohydrate-Modifying Biocatalysts 2016, 535

 


T. Walter, L. Collenburg, L. Japtok, B. Kleuser, S. Schneider-Schaulies, N. Müller, J. Becam, A. Schubert-Unkmeir, J. N. Konge, E. Bieberich and J. Seibel
Incorporation and visualization of azido-functionalized N-oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells
Chem. Commun. 2016, 52, 8612-8614


 


M. Ortiz-Soto, J. Seibel
Expression of Functional Human Sialyltransferases ST3Gal1 and ST6Gal1 in Escherichia coli
PLoS One 2016,  11, e0155410.

 


L. Collenburg, T. Walter, A. Burgert, N. Müller, J. Seibel, L. Japtok, B. Kleuser, M. Sauer, S. Schneider-Schaulies
A Functionalized Sphingolipid Analogue for Studying Redistribution during Activation in Living T Cells
J. Immunol. 2016, 196, 3951-3962.

 


M. Kraus, J. Görl, M. Timm, J. Seibel
Synthesis of the rare disaccharide nigerose by structure-based design of a phosphorylase mutant with altered regioselectivity
Chem. Commun. 2016, 52, 4625-4627.

 


M. Gutmann, E. Memmel, A. Braun, J. Seibel, L. Meinel, T. Lühmann
Biocompatible azide alkyne"click" reactions for surface decoration of glyco-engineered cells


ChemBioChem 2016, 17, 866-875. 


M. Kraus, C. Grimm, J. Seibel
Redesign of the active site of sucrose phosphorylase by a clash induced cascade of loop shifts


ChemBioChem 2016, 17, 33–36.


C. Fleck, E. Memmel, M. Fölsing, B. Poll, T. Hackl, J. Seibel, W. Maison
Synthesis and evaluation of neoglycoconjugates based on adamantyl scaffolds.
Eur. J. Org. Chem. 2015, 8, 1696–1710.


E. Memmel, J. Seibel
Metabolic Engineering of Bacteria.
in Proceedings of the 3rd Beilstein Glyco-Bioinformatics Symposium 2013 (Herausgeber M. G. Hicks, C. Kettner, P. Seeberger)
Beilstein Institut, Frankfurt/Main 2014, 1-9.


D. Claes, E. Memmel, M. Holzapfel, J. Seibel, W. Maison
High-Affinity Carbohydrate Binding by Trimeric Benzoboroxoles Measured on Carbohydrate Arrays.


ChemBioChem 2014, 15, 2450–2457.


S. Letschert, A. Göhler, C. Franke, N. Bertleff-Zieschang, E. Memmel, S. Doose, J. Seibel, M. Sauer
Super-Resolution Imaging of Plasma Membrane Glycans.
Angew. Chem. Int. Ed. 2014, 53(41), 10921–10924.


U. T. Bornscheuer, K. Buchholz, J. Seibel
Enzymatic degradation of (ligno-)celluloses.
Angew. Chem. Int. Ed. 2014, 53(41), 10876–10893.


S. Bank, E. Heller, E. Memmel, J. Seibel, U. Holzgrabe, P. Kapková
Matrix-assisted laser desorption/ionization tandem mass spectrometry of N-glycans derivatized with isonicotinic hydrazide and its biotinylated form.
Rapid Commun. Mass Spectrom. 2014, 28(15), 1745–1756.

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M. E. Ortiz-Soto, J. Seibel
Biotechnological Synthesis and Transformation of Valuable Sugars in the Food and Pharmaceutical Industry.
Current Organic Chemistry 2014, 18, 964–986.