Chemical Biology of Carbohydrates

This group is located at the Helmholtz Institute for Pharmaceutical Research Saarland (HIPS)

Carbohydrates and glycoconjugates belong to the three major classes of biopolymers. Complex carbohydrates play important roles in biological recognition processes that are represented by the presence of dense glycoconjugate layers on cells known as the glycocalyx. Despite their importance, the study of carbohydrates suffers from limited methods for their synthesis and analysis contrary to nucleic acids or proteins.


Research articles

Calvert, M.; Mayer, C.; Titz, A.* An Efficient synthesis of 1,6-anhydromuramic acid from N-acetyl glucosamine. Beilstein J Org Chem 2017, in revision.

Sommer, R.; Makshakova, O. N.; Wohlschlager, T.; Hutin, S.; Marsh, M.; Titz, A., Künzler, M.; Varrot, A. X-ray structures of Tectonin 2 from Laccaria bicolor revealed specific binding sites for methylated glycans and a unique tetrameric assembly with unprecedented multivalency. Structure 2017, in revision.

Wagner, S.; Hauck, D.; Hoffmann, M.; Sommer, R.; Joachim, I.; Müller, R.; Imberty, A.; Varrot, A.; Titz, A.* Covalent lectin inhibition and application in bacterial biofilm imaging. 2017, Angewandte Chemie, in press., doi: 10.1002/ange.201709368

Beshr, G.; Sikandar, A.; Jemiller, E.-M.; Klymiuk, N.; Hauck, D.; Wagner, S.; Wolf, E.; Koehnke, J.*; Titz, A.* Photorhabdus luminescens lectin A (PllA) - a new probe for detecting α-galactoside-terminating glycoconjugates. J. Biol. Chem. 2017, in press, doi: 10.1074/jbc.M117.812792

Hu, Y.; Beshr, G.; Garvey, C. J.; Tabor, R. F.; Titz, A.; Wilkinson, B. L. Photoswitchable Janus Glycodendrimer Micelles as Multivalent Inhibitors of LecA and LecB from Pseudomonas aeruginosa. Colloids Surf. B Biointerfaces  2017, 159, 605-612.

Sommer, R.; Hauck, D.; Titz, A.* Efficient two step β-glycoside synthesis from N-acetyl D-glucosamine: scope and limitations of copper(II) triflate-catalyzed glycosylation. ChemistrySelect 2017, 2, 4187-4192.

Torge, A.; Wagner, S.; Chaves, P.S.; Oliveira, E.G.; Guterres, S.S.; Pohlmann, A.R.; Titz, A.; Schneider, M.; Beck, R.C.R. Ciprofloxacin-loaded lipid-core nanocapsules as mucus penetrating drug delivery system intended for the treatment of bacterial infections in Cystic Fibrosis. Int. J. Pharm., 2017, 527(1–2), 92-102.

Joachim, I.; Rikker, S.; Hauck, D.; Ponader, D.; Boden, S.; Sommer, R.; Hartmann, L.; Titz, A.* Development and optimization of a competitive binding assay for the galactophilic low affinity lectin LecA from Pseudomonas aeruginosa. Org. Biomol. Chem. 2016, 14, 7933-7948.

Sommer, R.; Hauck, D.; Varrot, A.; Imberty, A.; Künzler, M.; Titz, A.* O-alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-l-selenofucoside. Beilstein J. Org. Chem., 2016, 12, 2828-2833.

Sommer, R.+; Wagner, S.+; Varrot, A.; Nycholat, C.; Khaledi, A.; Häussler, S.; Paulson, J.; Imberty, A.; Titz, A.* The virulence factor LecB varies in clinical isolates: consequences for ligand binding and drug design. Chem. Sci. 2016, 7, 4990-5001.

Beshr, G.+; Sommer, R.+; Hauck, D.; Siebert, D.C.B.; Hofmann, A.; Imberty, A.; Titz, A.* Development of a competitive binding assay for the Burkholderia cenocepacia lectin BC2L-A and structure activity relationship of natural and synthetic inhibitors. Med. Chem. Commun. 2016, 7, 519-530.

Sommer, R.; Hauck, D.; Varrot, A.; Wagner, S.; Prestel, A.; Möller, H.M.; Imberty, A.; Titz, A.* Cinnamide derivatives of D-mannose as inhibitors of the bacterial virulence factor LecB from Pseudomonas aeruginosa. ChemistryOpen 2015, 4(6), 756-767.

Yan, S.; Brecker, L.; Jin, C.; Titz, A.; Dragosits, M.; Karlsson, N.; Jantsch, V.; Wilson, I.B.H.; Paschinger, K. Bisecting galactose as a feature of N-glycans in wild-type and mutant Caenorhabditis elegans. Mol Cell Proteomics 2015, 14, 2111-2125.

Hofmann, A.+; Sommer, R.+; Hauck, D.; Stifel, J.; Göttker-Schnetmann, I.; Titz, A.* Synthesis of Mannoheptose Derivatives and their Evaluation as Inhibitors of the Lectin LecB from the Opportunistic Pathogen Pseudomonas aeruginosa. Carbohydr. Res. 2015, 412, 34-42.

Wohlschlager, T.; Butschi, A.; Grassi, P.; Sutov, G.; Gauss, R.; Hauck, D.; Schmieder, S.; Knobel, M.; Titz, A.; Dell, A.; Haslam, S.M.; Hengartner, M.O.; Aebi, M.; Künzler, M. Methylated glycans as conserved targets of animal and fungal innate defense against bacteria and nematodes. Proc. Natl. Acad. Sci. USA 2014, 111:E2787–E2796.

Mosca,S.; Keller, J.; Azzouz, N.; Wagner, S.; Titz, A.; Seeberger, P.H.; Brezesinski, G.; Hartmann, L. Amphiphilic cationic β3R3-peptides: membrane active peptidomimetics and their potential as antimicrobial agents. Biomacromolecules 2014, 15 (5), 1687–1695.

Sommer, R.; Exner, T.E.; Titz, A*. A Biophysical Study with Carbohydrate Derivatives Explains the Molecular Basis of Monosaccharide Selectivity of the Pseudomonas aeruginosa Lectin LecB PLoS ONE 2014, 9(11): e112822.

Hauck, D.+; Joachim, I.+; Frommeyer, B.+; Varrot, A.; Philipp, B.; Möller, H.M.; Imberty, A.; Exner, T.E.; Titz, A.* Discovery of two classes of potent glycomimetic inhibitors of Pseudomonas aeruginosa LecB with distinct binding modes ACS Chem. Biol. 2013, 8(8), 1775–1784.

Titz, A., Marra, A., Cutting, B., Smieško, M., Papandreou, G., Dondoni, A. and Ernst, B. Conformational Constraints: Nature Does It Best with Sialyl Lewisx. Eur. J. Org. Chem. 2012, 5534–5539.

Butschi, A.+; Titz, A.+; Walti, M.+; Oleric, V.; Paschinger,, K.; Guo, X.; Nöbauer, K.; Seeberger, P.; Wilson, I.B.H.; Hengartner, M.O.; Aebi, M.; Künzler, M. Caenorhabditis elegans N-glycan core β-galactoside confers sensitivity towards nematotoxic fungal galectin CGL2 PLoS Pathogens 2010, 6(1): e1000717. doi:10.1371/journal.ppat.1000717. + contributed equally

Titz, A.; Patton, J.; Smiesko, M.; Radic, Z.; Schwardt, O.; Magnani, J.L.; Ernst, B. Probing the Carbohydrate Recognition Domain of E-Selectin: The Importance of the Acid Orientation in sLex Mimetics Bioorg. Med. Chem. 2010, 18(1), 19.

Titz, A.+; Butschi, A.+; Henrissat, B.; Fan, Y.-Y.; Hennet, T.; Razzazi-Fazeli, E.; Hengartner, M.O.; Wilson, I.B.H.; Künzler, M.; Aebi, M. Molecular basis for galactosylation of core fucose residues in invertebrates: Identification of Caenorhabditis elegans N-glycan core α-1,6 fucoside β-1,4-galactosyl-transferase GALT-1 as a member of a novel glycosyltransferase family J. Biol. Chem. 2009, 284(52), 36223. + contributed equally

Titz, A.; Patton, J.; Alker, A.; Porro, M.; Schwardt, O.; Hennig, M.; Francotte, E.; Magnani, J.; Ernst, B. Is adamantane a suitable substituent to pre-organize the acid orientation in E-selectin antagonists? Bioorg. Med. Chem. 2008, 16, 1046.

Ramic, E.; Eichel, R.-A.; Dinse, K.-P.; Titz, A.; Schmidt, B. Complexation of copper(II)-chelidamate: multifrequency-pulsed electron paramagnetic resonance and electron nuclear double resonance analysis J. Phys. Chem. B 2006, 110, 20655 - 20663.

Titz, A.; Radic, Z.; Schwardt, O.; Ernst, B. A safe and convenient method for the preparation of triflyl azide, and its use in diazo transfer reactions to primary amines Tetrahedron Lett. 2006, 47, 2383 - 2385.

Deffieux, D.; Fabre, I.; Titz, A.; Leger, J.-M.; Quideau, S. Electrochemical synthesis of dimerizing and nondimerizing orthoquinone monoketals J. Org. Chem. 2004, 69, 8731 - 8738.

Schmidt, B.; Jiricek, J.; Titz, A.; Ye, G.; Parang, K. Copper dipicolinates as peptidomimetic ligands for the src SH2 domain Bioorg. Med. Chem. Lett. 2004, 14(16), 4203-4206.


Reviews and book chapters

Wagner, S.+; Sommer, R.+; Hinsberger, S.; Lu, C.; Hartmann, R.W.; Empting, M.*; Titz, A.* Novel Strategies for the treatment of P. aeruginosa infections. J. Med. Chem. 2016, 59 (13), 5929-5969.

Rodrigues, J.A.; Acosta-Serrano, A.; Aebi, M.; Ferguson, M.A.J.; Routier, F.H.; Schiller, I.; Soares, S.; Spencer, D.; Titz, A.; Wilson, I.B.H.; Izquierdo, L. Parasite glycobiology: A bittersweet symphony. PLoS Pathogens 2015, 11(11): e1005169.

Titz, A*, Carbohydrate-Based Anti-Virulence Compounds Against Chronic Pseudomonas aeruginosa Infections with a Focus on Small Molecules Top. Med. Chem. Springer Berlin Heidelberg. 2014, 12, 169-186.

Sommer, R.; Joachim, I.; Wagner, S.; Titz, A*. New Approaches to Control Infections: Anti-Biofilm Strategies against Gram-Negative Bacteria. CHIMIA 2013, 286-290.

Titz, A*. Biofilme Neue Forschungsansätze zur Therapie bakterieller Infektionskrankheiten GIT Labor-Fachzeitschrift 2013, (2) 120-121.

Titz, A.; Ernst, B. Mimetics of Sialyl Lewisx: The Pre-Organization of the Carboxylic Acid is Essential for Binding to Selectins. CHIMIA 2007, 61, 194.



Sommer, R.; Titz, A, Inhibitors of Pseudomonas aeruginosa LecB. WO2016/151066 A1. 

Titz, A. Glycomimetics as Pseudomonas aeruginosa lectin inhibitors. WO2013/152848 A1, granted patent.

Titz, A., Butschi, A., Aebi, M., Wilson, I.B.H., Hengartner, M., Künzler, M. Core beta-galactosyltransferase and uses thereof Patent. WO2010/136209 A1, granted patent.



Titz, A. E-selectin and the Natural Tetrasaccharide Ligand sialyl Lewisx: The Importance of Pharmacophore Pre-Organization in Glyco-Mimetics, Dissertation, Universität Basel, 2008. Online available at


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