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.



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.

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, doi: 10.1039/C6OB01313A.

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 discovery. Chemical Science 2016, 7, 4990-5001. accepted.

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. in press, DOI: 10.1039/c5md00557d.

Wagner, S.+; Sommer, R.+; Hinsberger, S.; Lu, C.; Hartmann, R. W.; Empting, E.*; Titz, A.* Novel strategies for the treatment of Pseudomonas aeruginosa infections. J. Med. Chem., 2016, 59 (13), 5929-5969. in press, DOI: 10.1021/acs.jmedchem.5b01698.


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.

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.

Sommer, R.; Titz, A. patent application. priority date 24 March 2015.

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. Carbohydrate Research 2015, 412, 34-42. accepted.

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.

Titz, A.* Carbohydrate-Based Anti-Virulence Compounds Against Chronic Pseudomonas aeruginosa Infections with a Focus on Small Molecules Top. Med. Chem. 2014, doi: 10.1007/7355_2014_44.

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.

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.

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

Titz, A., Biofilme Neue Forschungsansatze zur Therapie bakterieller Infektionskrankheiten GIT Labor-Fachzeitschrift 2013, 120-121.

Titz, A.; Marra, A.; Cutting, B.; Smiesko, M.; Papandreou, G.; Dondoni, A.; Ernst, B. Conformational constraints: Nature does it best with sialyl Lewisx Eur. J. Org. Chem. 2012, 5534-5539.

Titz, A. Glycomimetics as Pseudomonas aeruginosa lectin inhibitors. patent application. EP 12 002 531.7 and PCT/EP 2013/001047.

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.

Titz, A.; Patton, J.; Smiesko, M.; Radic, Z.; Schwardt, O.; Magnani, J.L.; Ernst, B. Probing theCarbohydrate 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.

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

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. 

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

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.

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

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

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

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