Publications
Kaiser, F., Endeward, B., Collauto, A., Scheffer, U., Prisner, T.F., and Göbel, M.W. (2022). Spin-Labeled Riboswitch Synthesized from a Protected TPA Phosphoramidite Building Block. Chem.--Eur. J. DOI:10.1002/chem.202201822
Hornung, J.-E., Weinrich, T., and Göbel, M.W. (2022). Directed Crosslinking of RNA by Glutathione‐Triggered PNA‐Quinone‐Methide‐Conjugates. Eur. J. Org. Chem.
DOI:10.1002/ejoc.202200318
Goldberg, M., Nakajima, M., Bolte, M., and Göbel, M.W. (2022). Facile conversion of 1,2-dicyanobenzene into chiral bisamidines. Arkivoc 2021, 225-238.
DOI:10.24820/ark.5550190.p011.722
Danneberg, F., Westemeier, H., Horx, P., Zellmann, F., Dörr, K., Kalden, E., Zeiger, M., Akpinar, A., Berger, R., and Göbel, M.W. (2021). RNA Hydrolysis by Heterocyclic Amidines and Guanidines: Parameters Affecting Reactivity. Eur. J. Org. Chem.
DOI: 10.1002/ejoc.202100950
Bolz, M., Scheffer, U., Kalden, E., Göbel, M. W. (2021). Redirection of the Transcription Factor SP1 to AT Rich Binding Sites by a Synthetic Adaptor Molecule. Helv. Chim. Acta.
DOI: 10.1002/hlca.202100095
Sreeramulu, S., Richter, C., Berg, H., Wirtz Martin, M.A., Ceylan, B., Matzel, T., Adam, J., Altincekic, N., Azzaoui, K., and Bains, J.K., Blommers, M. J. J., Ferner, J., Fürtig, B., Göbel, M., Grün, J. T., Hengesbach, M., Hohmann, K. F., Hymon, D., Knezic, B., Martins, J., Mertinkus, K. R., Niesteruk, A., Peter, S. A., Pyper, D. J., Qureshi, N. S., Scheffer, U., Schlundt, A., Schnieders, R., Stirnal, E., Sudakov, A., Tröster, A., Vögele, J., Wacker, A., Weigand, J. E., Wirmer-Bartoschek, J., Wöhnert, J. and Schwalbe, H. (2021). Exploring the druggability of conserved RNA regulatory elements in the SARS‐CoV‐2 genome. Angew. Chem. 60, 19191-19200.
DOI:10.1002/anie.202103693
Bolz, M., Thomas, L., Scheffer, U., Kalden, E., Hartmann, R.K., and Goebel, M.W. (2020). Redirection of miRNA-Argonaute Complexes to Specific Target Sites by Synthetic Adaptor Molecules. Chem. Biodiversity 17, e2000272.
DOI:10.1002/cbdv.202000272
Zellmann, F., and Goebel, M.W. (2020). A trisbenzimidazole phosphoramidite building block enables high-yielding syntheses of RNA-cleaving oligonucleotide conjugates. Molecules 25, 1842. DOI:10.3390/molecules25081842
Hornung, J.-E., Hellwig, N., and Goebel, M.W. (2020). Peptide Nucleic Acid Conjugates of Quinone Methide Precursors Alkylate Ribonucleic Acid after Activation with Light. Bioconjugate Chem. 31, 639-645.
DOI:10.1021/acs.bioconjchem.9b00796
Zellmann, F.; Thomas, L.; Scheffer, U.; Hartmann, R. K.; Göbel, M. W. (2019). Site-Specific Cleavage of RNAs Derived from the PIM1 3′-UTR by a Metal-Free Artificial Ribonuclease. Molecules 24, 807
DOI:10.3390/molecules24040807
Weinrich, T.; Jaumann, E.A.; Scheffer, U.; Prisner, T.F.; Göbel, M.W. (2018). A Cytidine Phosphoramidite with Protected Nitroxide Spin Label: Synthesis of a Full-Length TAR RNA and Investigation by In-Line Probing and EPR Spectroscopy. Chemistry 24, 6202–6207.
DOI:10.1002/chem.201800167
Weinrich, T.; Jaumann, E.A.; Scheffer, U.M.; Prisner, T.F.; Goebel, M.W. (2018). Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA. Beilstein J. Org. Chem. 14, 1563–156.
DOI:10.3762/bjoc.14.133
Weinrich, T., Gränz, M., Grünewald, C., Prisner, T. F., and Göbel, M. W. (2017). Synthesis of a Cytidine Phosphoramidite with Protected Nitroxide Spin Label for EPR Experiments with RNA. Eur. J. Org. Chem. 491–496.
https://doi.org/10.1002/ejoc.201601174
Stark, T. Lieblein, T. Pohland, M. Kalden, E. Freund, P. Zangl, R. Grewal, R. Heilemann, M. Eckert, G.P. Morgner, N. Goebel, M.W. (2017). Peptidomimetics that inhibit and partially reverse the Aggregation of Aβ1-42. Biochemistry, 56, 4840.
DOI: 10.1021/acs.biochem.7b00223
Goldberg, M., Sartakov, D., Bats, J.W., Bolte, M., and Göbel, M.W. (2016). A chiral analog of the bicyclic guanidine TBD. Synthesis, structure and Brønsted base catalysis. Beilstein J. Org. Chem. 12, 1870-1876.
DOI:10.3762/bjoc.12.176
Wirth-Hamdoune, D., Ullrich, S., Scheffer, U., Radanović, T., Duerner, G., and Goebel, M.W. (2016). A Bis(guanidinium)alcohol Attached to a Hairpin Polyamide: Synthesis, DNA Binding, and Plasmid Cleavage. ChemBioChem 17, 506-514.
DOI:10.1002/cbic.201500566
Dogandzhiyski, P., Ghidini, A., Danneberg, F., Stromberg, R., and Gobel, M.W. (2015). Studies on tris(2-aminobenzimidazole)-PNA based artificial nucleases: a comparison of two analytical techniques. Bioconjugate Chem. 26, 2514-2519.
DOI:10.1021/acs.bioconjchem.5b00534
Danneberg, F., Ghidini, A., Dogandzhiyski, P., Kalden, E., Strömberg, R., and Göbel, M.W. (2015). Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole). Beilstein J. Org. Chem. 11, 493-498.
DOI:10.3762/bjoc.11.55
Zeiger, M., Stark, S., Kalden, E., Ackermann, B., Ferner, J., Scheffer, U., Shoja-Bazargani, F., Erdel, V., Schwalbe, H., and Göbel, M.W. (2014). Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR. Bioorg. Med. Chem. Lett.
DOI:10.1016/j.bmcl.2014.11.004
Seven, I., Weinrich, T., Gränz, M., Grünewald, C., Brüß, S., Krstić, I., Prisner, T.F., Heckel, A., and Göbel, M.W. (2014). Photolabile Protecting Groups for Nitroxide Spin Labels. Eur. J. Org. Chem. 19 4037-4043
DOI:10.1002/ejoc.201301692
Stark, T., Suhartono, M., Göbel, M. W., and Lautens, M. (2013). A Palladium-Catalyzed Domino Reaction as Key Step for the Synthesis of Functionalized Aromatic Amino Acids. Synlett 24, 2730–2734.
https://doi.org/10.1055/s-0033-1339892
Cernescu, M.; Stark, T.; Kalden, E.; Kurz, C.; Leuner, K.; Deller, T.; Göbel, M.; Eckert, G. P.; Brutschy, B. (2012). Laser-Induced Liquid Bead Ion Desorption Mass Spectrometry: An Approach to Precisely Monitor the Oligomerization of the β-Amyloid Peptide. Anal. Chem. 84 5276–5284
DOI: 10.1021/ac300258m
Pinto Gomes, C.; Metz, A.; Bats, J. W.; Gohlke, H.; Göbel, M. W. (2012). Modular Solid-Phase Synthesis of Teroxazoles as a Class of α-Helix Mimetics. Eur. J. Org. Chem. 3270–3277
DOI: 10.1002/ejoc.201200339
Nosenko, Y.; Kunitski, M.; Stark, T.; Göbel, M.; Tarakeshwar, P.; Brutschy, B. (2011). 4-Aminobenzimidazole–1-Methylthymine: A Model for Investigating Hoogsteen Base-Pairing between Adenine and Thymine. J. Phys. Chem. A 115 11403–11411
DOI: 10.1021/jp205575w
Ullrich, S., Nazir, Z., Büsing, A., Scheffer, U., Wirth, D., Bats, J.W., Dürner, G. and Göbel, M. W. (2011). Cleavage of Phosphodiesters and of DNA by a Bis(guanidinium)naphthol Acting as a Metal-Free Anion Receptors. ChemBioChem 12, 1223-1229
DOI: 10.1002/cbic.201100022
Weimar, M., Dürner, G., Bats, J. W., and Göbel, M. W. (2010). Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels-Alder Reaction. J. Org. Chem. 75, 2718-2721.
https://doi.org/10.1021/jo100053j
Suhartono, M., Schneider, A. E., Duerner, G., and Goebel, M. W. (2010). Synthetic aromatic amino acids from a Negishi cross-coupling reaction. Synthesis, 293-303.
https://doi.org/10.1055/s-0029-1217124
Sreeramulu, S., Gande, S. L., Goebel, M., and Schwalbe, H. (2009). Molecular Mechanism of Inhibition of the Human Protein Complex Hsp90-Cdc37, a Kinome Chaperone-Cochaperone, by Triterpene Celastrol. Angew. Chem., Int. Ed. 48, 5853-5855.
DOI: 10.1002/anie.200900929
Ferner, J., Suhartono, M., Breitung, S., Jonker, H. R. A., Hennig, M., Woehnert, J., Goebel, M., and Schwalbe, H. (2009). Structures of HIV TAR RNA-Ligand Complexes Reveal Higher Binding Stoichiometries. ChemBioChem 10, 1490-1494.
https://doi.org/10.1002/cbic.200900220
Breitung, S. T., Lopez, J. J., Duerner, G., Glaubitz, C., Goebel, M. W., and Suhartono, M. (2008). A practical synthesis of the 13C/15N-labeled tripeptide N-Formyl-Met-Leu-Phe, useful as a reference in solid-state NMR spectroscopy. Beilstein J. Org. Chem. 4, No. 35.
https://doi.org/10.3762/bjoc.4.35
Morgner, N., Barth, H.-D., Brutschy, B., Scheffer, U., Breitung, S., and Goebel, M. (2008). Binding sites of the viral RNA element TAR and of TAR mutants for various peptide ligands, probed with LILBID: A new laser mass spectrometry. J. Am. Soc. Mass. Spectrom. 19, 1600-1611.
https://doi.org/10.1016/j.jasms.2008.07.001
Akalay, D., Duerner, G., and Goebel, M. W. (2008). A first case of asymmetric catalysis induced by metal-free bisoxazolines. Eur. J. Org. Chem., 2365-2368.
https://doi.org/10.1002/ejoc.200800179
Schueller, A., Suhartono, M., Fechner, U., Tanrikulu, Y., Breitung, S., Scheffer, U., Goebel, M. W., and Schneider, G. (2008). The concept of template-based de novo design from drug-derived molecular fragments and its application to TAR RNA. J. Comput.-Aided Mol. Des. 22, 59-68.
DOI: 10.1007/s10822-007-9157-4
Suhartono, M., Weidlich, M., Stein, T., Karas, M., Duerner, G., and Goebel, M. W. (2008). Synthesis of non-natural aromatic alpha -amino acids by a Heck reaction. Eur. J. Org. Chem., 1608-1614.
https://doi.org/10.1002/ejoc.200701124
Akalay, D., Duerner, G., Bats, J. W., and Goebel, M. W. (2008). C2-symmetric bisamidines: chiral Bronsted bases catalysing the Diels-Alder reaction of anthrones. Beilstein J. Org. Chem. 4, No. 28.
https://doi.org/10.3762/bjoc.4.28
Morgner, N., Barth, H. D., Schmidt, T. L., Heckel, A., Scheffer, U., Goebel, M., Fucini, P., and Brutschy, B. (2007). Detecting specific ligand binding to nucleic acids: a test for ultrasoft laser mass spectrometry. Z. Phys. Chem. 221, 689-704.
DOI: 10.1524/zpch.2007.221.5.689
Akalay, D., Duerner, G., Bats, J. W., Bolte, M., and Goebel, M. W. (2007). Synthesis of C2-Symmetric Bisamidines: A New Type of Chiral Metal-Free Lewis Acid Analogue Interacting with Carbonyl Groups. J. Org. Chem. 72, 5618-5624.
https://doi.org/10.1021/jo070534j
Tanrikulu, Y., Nietert, M., Scheffer, U., Proschak, E., Grabowski, K., Schneider, P., Weidlich, M., Karas, M., Goebel, M., and Schneider, G. (2007). Scaffold hopping by fuzzy pharmacophores and its application to RNA targets. ChemBioChem 8, 1932-1936.
DOI: 10.1002/cbic.200700195
Ludwig, V., Krebs, A., Stoll, M., Dietrich, U., Ferner, J., Schwalbe, H., Scheffer, U., Durner, G., and Gobel, M. W. (2007). Tripeptides from synthetic amino acids block the Tat-TAR association and slow down HIV spread in cell cultures. Chembiochem 8, 1850-1856.
https://doi.org/10.1002/cbic.200700232
Givehchi, A., Ludwig, V., Boden, O., Krebs, A., Scheffer, U., Goebel, M., and Schneider, G. (2007). Classification and prediction of tripeptides inhibiting HIV-1 Tat/TAR-RNA interaction using a self-organizing map. Lett. Drug Des. Discovery 4, 410-416.
http://dx.doi.org/10.2174/157018007781387791
Nandi, C. K., Parui, P. P., Brutschy, B., Scheffer, U., and Goebel, M. (2007). Fluorescence correlation spectroscopy at single molecule level on the Tat-TAR complex and its inhibitors. Biopolymers 89, 17-25.
DOI: 10.1002/bip.20835
Gnaccarini, C., Peter, S., Scheffer, U., Vonhoff, S., Klussmann, S., and Goebel, M. W. (2006). Site-Specific Cleavage of RNA by a Metal-Free Artificial Nuclease Attached to Antisense Oligonucleotides. J. Am. Chem. Soc. 128, 8063-8067.
https://doi.org/10.1021/ja061036f
Scheffer, U., Strick, A., Ludwig, V., Peter, S., Kalden, E., and Gobel, M. W. (2005). Metal-free catalysts for the hydrolysis of RNA derived from guanidines, 2-aminopyridines, and 2-aminobenzimidazoles. J. Am. Chem. Soc. 127, 2211-2217.
https://doi.org/10.1021/ja0443934
Scheffer, U., and Göbel, M. (2005). Fluorescence-Based On-Line Detection as an Analytical Tool in RNA Electrophoresis. Methods Mol. Biol. (N. Y.) 288, 261-272.
DOI: 10.1385/1-59259-823-4:261
Hey, M., and Goebel, M. (2005). Non-enzymatic template-directed RNA synthesis. Methods Mol. Biol. (N. Y.) 288, 305-318.
DOI: 10.1385/1-59259-823-4:305
Renner, S., Ludwig, V., Boden, O., Scheffer, U., Göbel, M., and Schneider, G. (2005). New Inhibitors of the Tat–TAR RNA Interaction Found with a “Fuzzy” Pharmacophore Model. ChemBioChem 6, 1119-1125.
DOI: 10.1002/cbic.200400376
Riguet, E., Desire, J., Boden, O., Ludwig, V., Goebel, M., Bailly, C., and Decout, J.-L. (2005). Neamine dimers targeting the HIV-1 TAR RNA. Bioorg. Med. Chem. Lett. 15, 4651-4655.
DOI: 10.1016/j.bmcl.2005.07.082
Krebs, A., Ludwig, V., Pfizer, J., Durner, G., and Gobel, M. W. (2004). Enantioselective synthesis of non-natural aromatic alpha-amino acids. Chemistry 10, 544-553.
https://doi.org/10.1002/chem.200305421
Hey, M., Hartel, C., and Göbel, M. W. (2003). Nonenzymatic oligomerization of ribonucleotides: Towards in vitro selection experiments. Helv. Chim. Acta 86, 844-854.
https://doi.org/10.1002/hlca.200390084
Krebs, A., Ludwig, V., Boden, O., and Göbel, M. W. (2003). Targeting the HIV Trans-Activation Responsive Region–Approaches Towards RNA-Binding Drugs. ChemBioChem 4, 972-978.
DOI: 10.1002/cbic.200300652
Pitsch, S., Scheffer, U., Hey, M., Strick, A., and Göbel, M. W. (2003). On Facts and Artefacts: The Difficulty to Evaluate an Artificial Nuclease. Helv. Chim. Acta 86, 7340-3752.
https://doi.org/10.1002/hlca.200390316
Schwalbe, H.; Göbel, M.; Wess, G. (2003). Editorial: RNA Targeting. ChemBioChem 4, 915-917
https://doi.org/10.1002/cbic.200300744
Tsogoeva, S. B., Dürner, G., Bolte, M., and Göbel, M. W. (2003). A C2-chiral bis(amidinium) catalyst for a Diels-Alder reaction constituting the key step of the Quinkert-Dane estrone synthesis. Eur. J. Org. Chem., 1661-1664.
https://doi.org/10.1002/ejoc.200200635
Scarso, A., Scheffer, U., Gobel, M., Broxterman, Q. B., Kaptein, B., Formaggio, F., Toniolo, C., and Scrimin, P. (2002). A peptide template as an allosteric supramolecular catalyst for the cleavage of phosphate esters. Proc. Natl. Acad. Sci.U. S. A. 99, 5144-5149.
DOI: 10.1073/pnas.072642699
Hartel, C., and Göbel, M. W. (2000). Substitution of adenine by purine-2,6-diamine improves the non-enzymic oligomerization of ribonucleotides on templates containing thymidine. Helv. Chim. Acta 83, 2541-2549.
https://doi.org/10.1002/1522-2675(20000906)83:9%3C2541::AID-HLCA2541%3E3.0.CO;2-8
Schuster, T., Kurz, M., and Goebel, M. W. (2000). Catalysis of a Diels-Alder Reaction by Amidinium Ions. J. Org. Chem. 65, 1697-1701.
https://doi.org/10.1021/jo991372x
Schuster, T., Bauch, M., Duerner, G., and Goebel, M. W. (2000). Axially Chiral Amidinium Ions as Inducers of Enantioselectivity in Diels-Alder Reactions. Org. Lett. 2, 179-181.
https://doi.org/10.1021/ol991276i
Schuster, T., and Gobel, M. W. (1999). Synthesis of a chiral receptor molecule with converging amidinium and hydroxy groups. Synlett., 966-968.
https://doi.org/10.1055/s-1999-3095
Kurz, M., Göbel, K., Hartel, C., and Göbel, M. W. (1998). Acridine-labeled primers as tools for the study of nonenzymatic RNA oligomerization. Helv. Chim. Acta 81.
https://doi.org/10.1002/hlca.19980810528
Kurz, M., Göbel, K., Hartel, C., and Göbel, M. W. (1997). Nonenzymic oligomerization of ribonucleotides on guanosine-rich templates: suppression of the self-pairing of guanosine. Angew. Chem., Int. Ed. Engl. 36, 842-845.
https://doi.org/10.1002/anie.199708421
Muche, M.-S., Kamalaprija, P., and Gobel, M. W. (1997). Reaction cascade in the supramolecular phosphorylation of a bis(guanidinium) diol. Tetrahedron Lett. 38, 2923-2926.
https://doi.org/10.1016/S0040-4039(97)00513-3
Kurz, K., and Goebel, M. W. (1996). Hydrolytical cleavage of TAR-RNA, the trans-activation responsive region of HIV-1, by a bis(guanidinium) catalyst attached to arginine. Helv. Chim. Acta 79, 1967-1979.
https://doi.org/10.1002/hlca.19960790719
Muche, M.-S., and Goebel, M. W. (1996). Bis(guanidinium) alcohols as models of staphylococcal nuclease: substrate binding through ion pair complexes and fast phosphoryl transfer reactions. Angew. Chemie, Int. Ed. Engl. 35, 2126-2129.
https://doi.org/10.1002/anie.199621261
Schuetz, K., Kurz, M., and Goebel, M. W. (1995). Synthesis of oligodeoxyribonucleotides labeled with a novel type of chemically stable acridine dye. Tetrahedron Lett. 36, 8407-8410.
https://doi.org/10.1016/0040-4039(95)01801-N
Reckenbeil, D., Bats, J. W., Duerner, G., and Goebel, M. W. (1994). Supramolecular phosphorylation of cationic alcohols with a 3-arylindole-4-carboxyamidine framework. Liebigs Ann. Chem., 1219-1229.
https://doi.org/10.1002/jlac.199419941213
Mueller, G., Duerner, G., Bats, J. W., and Goebel, M. W. (1994). Supramolecular phosphoryl transfer reactions mediated by amidinium phosphate ion-pair complexes. Liebigs Ann. Chem., 1075-1092.
https://doi.org/10.1002/jlac.199419941106
Goebel, M. W. (1994). Binuclear metal complexes as efficient mediators of biochemically relevant hydrolysis reactions. Angew. Chem. 106, 1201-1203
DOI: 10.1002/anie.199411411
Lehr, S., Schuetz, K., Bauch, M., and Goebel, M. W. (1994). Axial-chiral amidinium ions with biaryl framework: a new structure type for host-guest chemistry. Angew. Chem. 106, 1041-1043
https://doi.org/10.1002/anie.199409841
Gross, R., Bats, J. W., and Goebel, M. W. (1994). trans-Decalin as a spacer for axially configurated diamines: preparation of a phosphate binding bis(guanidinium) compound. Liebigs Ann. Chem., 205-210.
https://doi.org/10.1002/jlac.199419940215
Gross, R., Duerner, G., and Goebel, M. W. (1994). Acceleration of substitution reactions of a phosphoric acid diester by bis(guanidinium) compounds. Liebigs Ann. Chem., 49-58.
https://doi.org/10.1002/jlac.199419940110
Hunziker, J., Roth, H. J., Boehringer, M., Giger, A., Diederichsen, U., Goebel, M., Krishnan, R., Jaun, B., Leumann, C., and Eschenmoser, A. (1993). Why pentose- and not hexose-nucleic acids? Part III. Oligo(2',3'-dideoxy-b-D-glucopyranosyl)nucleotides. ('Homo-DNA'): base-pairing properties. Helv. Chim. Acta 76, 259-352.
https://doi.org/10.1002/hlca.19930760119
Goebel, M. W., Bats, J. W., and Duerner, G. (1992). Approaches to synthetic phosphodiesterases: supramolecular phosphoryl transfer mediated by amidinium phosphate contact ion pairs. Angew. Chem. 104, 217-218.
https://doi.org/10.1002/anie.199202071
Boehringer, M., Roth, H. J., Hunziker, J., Goebel, M., Krishnan, R., Giger, A., Schweizer, B., Schreiber, J., Leumann, C., and Eschenmoser, A. (1992). Why pentose and not hexose nucleic acids? Part II. Preparation of oligonucleotides containing 2',3'-dideoxy-b-D-glucopyranosyl building blocks. Helv. Chim. Acta 75, 1416-1477.
https://doi.org/10.1002/hlca.19920750503
Leumann, C., Frueh, T., Goebel, M., and Eschenmoser, A. (1987). Chemistry of pyrrocorphines. Biomimetic regioselectivity of C-methylation on the ligand periphery of magnesium(II) uropyrrocorphinate octanitriles of type 1. Angew. Chem. 99, 273-275.
DOI: 10.1002/anie.198702611