Publications 

2024

Enhanced TROSY Effect in [2-¹⁹F, 2-¹³C] Adenosine and ATP Analogs Facilitates NMR Spectroscopy of Very Large Biological RNAs in Solution
F. Juen, D. Glänzer, R. Plangger, V. Kugler, J. Fleischmann, E. Stefan, D. A. Case, H. Kovacs, T. Kwaku Dayie, C. Kreutz.
Angew Chem Int Ed Engl. 2024 Feb 26;63(9):e202316273. doi: 10.1002/anie.202316273.  link

2023

Extending the toolbox for RNA biology with SegModTeX: a polymerase-driven method for site-specific and segmental labeling of RNA.
Haslecker R, Pham VV, Glänzer D, Kreutz C, Dayie TK, D'Souza VM.
Nat Commun. 2023 Dec 18;14(1):8422. doi: 10.1038/s41467-023-44254-3. link

Contribution of tRNA sequence and modifications to the decoding preferences of E. coli and M. mycoides tRNAGlyUCC for synonymous glycine codons.
Kompatscher M, Bartosik K, Erharter K, Plangger R, Juen FS, Kreutz C, Micura R, Westhof E, Erlacher MD.
Nucleic Acids Res. 2024 Feb 9;52(3):1374-1386. doi: 10.1093/nar/gkad1136. link

An Analysis of Nucleotide-Amyloid Interactions Reveals Selective Binding to Codon-Sized RNA.
Rout SK, Cadalbert R, Schröder N, Wang J, Zehnder J, Gampp O, Wiegand T, Güntert P, Klingler D, Kreutz C, Knörlein A, Hall J, Greenwald J, Riek R.
J Am Chem Soc. 2023 Oct 11;145(40):21915-21924. doi: 10.1021/jacs.3c06287. link

Advances in RNA Labeling with Trifluoromethyl Groups.
Eichler C, Himmelstoß M, Plangger R, Weber LI, Hartl M, Kreutz C, Micura R.
Chemistry. 2023 Oct 26;29(60):e202302220. doi: 10.1002/chem.20230222 link

Native Top-Down Mass Spectrometry Uncovers Two Distinct Binding Motifs of a Functional Neomycin-Sensing Riboswitch Aptamer.
Heel SV, Bartosik K, Juen F, Kreutz C, Micura R, Breuker K.
J Am Chem Soc. 2023 Jul 19;145(28):15284-15294. doi: 10.1021/jacs.3c02774. link

Measuring the Enthalpy of an Individual Hydrogen Bond in a DNA Duplex with Nucleobase Isotope Editing and Variable-Temperature Infrared Spectroscopy.
Peng HC, Castro GL, Karthikeyan V, Jarrett A, Katz MA, Hargrove JA, Hoang D, Hilber S, Meng W, Wang L, Fick RJ, Ahn JM, Kreutz C, Stelling AL.
J Phys Chem Lett. 2023 May 11;14(18):4313-4321. doi: 10.1021/acs.jpclett.3c00178 link

Multi-site conformational exchange in the synthetic neomycin-sensing riboswitch studied by ¹⁹F NMR.
Jan OH, Vögele J, Nussbaumer F, Duchardt-Ferner E, Kreutz C, Wöhnert J, Sprangers R.
Angew Chem Int Ed Engl. 2023 Jun 5;62(23):e202218064. doi: 10.1002/anie.202218064  link 

2022

Structural basis for recognition of transcriptional terminator structures by ProQ/FinO domain RNA chaperones.
Kim HJ, Black M, Edwards RA, Peillard-Fiorente F, Panigrahi R, Klingler D, Eidelpes R, Zeindl R, Peng S, Su J, Omar AR, MacMillan AM, Kreutz C, Tollinger M, Charpentier X, Attaiech L, Glover JNM.
Nat Commun. 2022 Nov 18;13(1):7076. doi: 10.1038/s41467-022-34875-5. link

Rapid and reliable RNA resonance assignment by combining chemical and enzymatic stable isotope labeling.
Klingler D, Huber M, Tollinger M, Kreutz C*.
Journal of Magnetic Resonance Open. 2022 Sep 26; 12-13:100077. doi: 10.1016/j.jmro.2022.100077. link

A Fluoroponytailed NHC-Silver Complex Formed from Vinylimidazolium/AgNO₃ under Aqueous-Ammoniacal Conditions.
Partl G, Rauter M, Fliri L, Gelbrich T, Kreutz C, Müller T, Kahlenberg V, Nerdinger S*, Schottenberger H*.
Molecules. 2022 Jun 28;27(13):4137. doi: 10.3390/molecules27134137. link

Towards a comprehensive understanding of RNA deamination: synthesis and properties of xanthosine-modified RNA.
Mair S, Erharter K, Renard E, Brillet K, Brunner M, Lusser A, Kreutz C*, Ennifar E*, Micura R*.
Nucleic Acids Res. 2022 Jun 10;50(11):6038-51. doi: 10.1093/nar/gkac477. link

1-Deazaguanosine-Modified RNA: The Missing Piece for Functional RNA Atomic Mutagenesis.
Bereiter R, Renard E, Breuker K, Kreutz C, Ennifar E, Micura R*.
J Am Chem Soc. 2022 Jun 15;144(23):10344-10352. doi: 10.1021/jacs.2c01877. link

Kehinde M. Taiwo, Lukasz T. Olenginski, Felix Nußbaumer, Hyeyeon Nam, Stefan Hilber, Christoph Kreutz and T. Kwaku Dayie*.
Synthesis of [7-¹⁵N]-GTPs for RNA structure and dynamics by NMR spectroscopy.
Monatshefte für Chemie - Chemical Monthly 2022; 153: 293–299. doi: 10.1007/s00706-022-02892-1. link

Neuner S, Schwartz HA, Kreutz C, Müller T, Mayer P, Bonn G, Gelbrich T, Griesser UJ, Wurst K, Kahlenberg V, Nerdinger S*, Schottenberger, H*.
2-Arylazoimidazoles Revamped by Quarternization or Dimerization; Another Gain in Functionality of an Industrial Dyestuff Family by Task-Specific Side-Chain Substituents.
Heterocycles 2022. 105(1): 461 - 476. doi: 10.3987/COM-22-S(R)17. link

Pann J, Erharter K, Langerreiter D, Partl G, Müller T, Schottenberger H, Hummel M, Hofer TS, Kreutz C*, Fliri L*.
Mechanistic Insights into the Formation of 1-Alkylidene/Arylidene-1,2,4-triazolinium Salts: A Combined NMR/Density Functional Theory Approach.
J Org Chem. 2022; 87(2): 1019-1031. doi: 10.1021/acs.joc.1c02327. link

2021

Oettl S, Bosello M, Marschall K, Gallmetzer A, Reyes-Dominguez Y, Kreutz C, Tollinger M, Robatscher P, Oberhuber M*.
(3ξ,4ξ,5ξ,6ξ,7ξ,11ξ)-3,6-dihydroxy-8-oxo-9-eremophilene- 12-oic acid, a new phytotoxin of alternaria alternata ssp. tenuissima isolates associated with fruit spots on apple (Malus × domestica Borkh.).
J. Agricult Food Chem 2021; 69(48): 14445–14458. doi: 10.1021/acs.jafc.1c02847. Online ahead of print. link 

A quantitative model predicts how m⁶A reshapes the kinetic landscape of nucleic acid hybridization and conformational transitions.
Liu B, Shi H, Rangadurai A, Nussbaumer F, Chu CC, Erharter KA, Case DA, Kreutz C, Al-Hashimi HM.
Nat Commun. 2021 Aug 31;12(1):5201. doi: 10.1038/s41467-021-25253-8. link

Probing the Hydrogen-Bonding Environment of Individual Bases in DNA Duplexes with Isotope-Edited Infrared Spectroscopy.
Fick RJ, Liu AY, Nussbaumer F, Kreutz C, Rangadurai A, Xu Y, Sommer RD, Shi H, Scheiner S, Stelling AL.
J Phys Chem B. 2021 Jul 22;125(28):7613-7627. doi: 10.1021/acs.jpcb.1c01351. link

Impact of 3-deazapurine nucleobases on RNA properties.
Bereiter R, Himmelstoß M, Renard E, Mairhofer E, Egger M, Breuker K, Kreutz C, Ennifar E, Micura R.
Nucleic Acids Res. 2021 May 7;49(8):4281-4293. doi: 10.1093/nar/gkab256. link

2020

Native mass spectrometry reveals the initial binding events of HIV-1 rev to RRE stem II RNA.
Schneeberger EM, Halper M, Palasser M, Heel SV, Vušurović J, Plangger R, Juen M, Kreutz C, Breuker K.
Nat Commun. 2020 Nov 13;11(1):5750. doi: 10.1038/s41467-020-19144-7. link

2'-O-Methylation can increase the abundance and lifetime of alternative RNA conformational states.
Abou Assi H, Rangadurai AK, Shi H, Liu B, Clay MC, Erharter K, Kreutz C, Holley CL, Al-Hashimi HM.
Nucleic Acids Res. 2020 Dec 2;48(21):12365-12379. doi: 10.1093/nar/gkaa928. link

2′-O-Trifluoromethylated RNA – A powerful modification for RNA chemistry and NMR spectroscopy.
M. Himmelstoß, K. Erharter, E. Renard, E. Ennifar,* C. Kreutz,* R. Micura*
Chem. Sci. 2020, 11, 11322-11330. link

Aromatic ¹⁹F-¹³C TROSY - [¹⁹F, ¹³C] pyrimidine labeling for NMR spectroscopy of RNA.
Nußbaumer F, Plangger R, Roeck M, Kreutz C.*
Angew Chem Int Ed Engl. 2020 Sep 21;59(39):17062-17069. doi: 10.1002/anie.202006577link 

N-Phenethyl Substitution in 14-Methoxy-N-methylmorphinan-6-ones Turns Selective µ Opioid Receptor Ligands into Dual µ/δ Opioid Receptor Agonists.
Dumitrascuta M, Bermudez M, Ben Haddou T, Guerrieri E, Schläfer L, Ritsch A, Hosztafi S, Lantero A, Kreutz C, Massotte D, Schmidhammer H, Wolber G, Spetea M.*
Sci Rep. 2020 Mar 27; 10(1): 5653. doi: 10.1038/s41598-020-62530-w. link

2019

NMR chemical exchange measurements reveal that N6-methyladenosine slows RNA annealing.
Shi H, Liu B, Nussbaumer F, Rangadurai A, Kreutz C*, Al-Hashimi HM.*
J. Am. Chem. Soc. (2019); 141(51): 19988-19993.  doi: 10.1021/jacs.9b10939. link

m⁶A minimally impacts the structure, dynamics, and Rev ARM binding properties of HIV-1 RRE stem IIB.
Chu CC, Liu B, Plangger R, Kreutz C, Al-Hashimi HM.*
PLoS One. (2019);14(12):e0224850. doi: 10.1371/journal.pone.0224850. link

Structure of an RNA aptamer in complex with the fluorophore tetramethylrhodamine.
Duchardt-Ferner E, Juen MA, Bourgeois B, Madl T, Kreutz C, Ohlenschläger O, Wöhnert J.*
Nucleic Acids Res. 2019, doi: 10.1093/nar/gkz1113.  link

Branch site bulge conformations in domain 6 determine functional sugar puckers in group II intron splicing.
Plangger R, Juen M, Hoernes T, Nußbaumer F, Kremser J, Strebitzer E, Klingler D, Erharter K, Tollinger M, Erlacher M, Kreutz C.*
Nucleic Acids Res. (2019); 47(21): 11430-11440. doi: 10.1093/nar/gkz965. link

Direct evidence for (G)O6···H₂-N4(C)⁺ hydrogen bonding in transient G(syn)-C⁺ and G(syn)-m⁵C⁺ Hoogsteen base pairs in duplex DNA from cytosine amino nitrogen off-resonance R_1ρ relaxation dispersion measurements.
Rangadurai A, Kremser J, Shi H, Kreutz C*, Al-Hashimi HM.*
J Magn Reson. 2019 Sep 5;308:106589. doi: 10.1016/j.jmr.2019.106589. link

Dynamic ensemble of HIV-1 RRE stem IIB reveals non-native conformations that disrupt the Rev-binding site.
Chu CC, Plangger R, Kreutz C, Al-Hashimi HM.
Nucleic Acids Res. 2019 Jun 14. pii: gkz498. doi: 10.1093/nar/gkz498. link

2018

Synthetic and structural studies on pentafluorobenzylated imidazole systems.
Lampl M, Schlapp-Hackl I, Wurst H, Gelbrich T, Kopacka H, Mueller T, Kreutz C, Naier B, Partl G*, Kahlenberg V, Amer H, Bacher M, Rosenau T, Huppertz H, Schottenberger H.
Journal of Fluorine Chemistry (2018);218: 51-62.

Translation of non-standard codon nucleotides reveals minimal requirements for codon-anticodon interactions.
Hoernes TP, Faserl K, Juen MA, Kremser J, Gasser C, Fuchs E, Shi X, Siewert A, Lindner H, Kreutz C, Micura R, Joseph S, Höbartner C, Westhof E, Hüttenhofer A, Erlacher MD*.
Nat Commun. (2018); doi: 10.1038/s41467-018-07321-8. link

The 5-oxyacetic acid modification destabilizes double helical stem structures and favors anionic Watson-Crick like cmo⁵U-G base pairs.
Strebitzer E^#, Rangadurai A^#, Plangger R, Kremser J, Juen MA, Tollinger M, Al-Hashimi H_^*, Kreutz C^*
Chemistry (2018); 24:18903-18906. link
^# These authors contributed equally.

Chlorophyll Breakdown in a Fern - Discovery of Carbon-Skeleton Rearranged Phyllobilin Isomers.
Erhart T, Vergeiner S, Kreutz C, Kräutler B^*, Müller T.^*
Angew Chem Int Ed Engl. (2018); 57(45): 14937-14941.

NMR resonance assignments for the SAM/SAH-binding riboswitch RNA bound to S-adenosylhomocysteine.
Weickhmann AK, Keller H, Duchardt-Ferner E, Strebitzer E, Juen MA, Kremser J, Wurm JP, Kreutz C, Wöhnert J.^*
Biomol NMR Assign. (2018); 12(2): 329-334. link

A potentially abundant junctional RNA motif stabilized by m⁶A and Mg²⁺.
Liu B, Merriman DK, Choi SH, Schumacher MA, Plangger R, Kreutz C, Horner SM, Meyer KD, Al-Hashimi HM.^*
Nat Commun. (2018); 9(1): 2761. link

Studying sparsely populated conformational states in RNA combining chemical synthesis and solution NMR spectroscopy.
Strebitzer E, Nußbaumer F, Kremser J, Tollinger M, Kreutz C.*
Methods (2018); 148: 39-47. link

Isotope labeling for studying RNA by solid-state NMR spectroscopy.
Marchanka A, Kreutz C, Carlomagno T.*
J. Biomol. NMR (2018); 71: 151-164. link

Residue and site-specific labeling of CCR5 RNA pseudoknot reveals internal motions that correlate with microRNA binding.
Chen B, Longhini AP, Nußbaumer F, Kreutz C, Dinman J*, Dayie TK.*
Chemistry - A European Journal (2018); 24(21):5462-5468. link

Atomic mutagenesis of stop codon nucleotides reveals the chemical prerequisites for release factor-mediated peptide release.
Hoernes TP, Clementi N, Juen MA, Shi X, Faserl K, Willi J, Gasser C, Kreutz C, Simpson J, Linder H, Huettenhofer A, Erlacher MD.*
Proc Natl Acad Sci U S A. (2018) ; 115(3): E382-E389. link

2017

Molecular basis for asymmetry sensing of siRNAs by the Drosophila Loqs-PD / Dcr-2 complex in RNA interference.
Tants JN, Fesser S, Kern T, Stehle R, Geerlof A, Wunderlich CH, Juen MA, Hartlmüller C, Böttcher R, Kunzelmann S, Lange O, Kreutz C, Förstemann K, Sattler M.*
Nucl. Acids Res. (2017); 45(21): 12536-12550. link

Chemical synthesis and NMR spectroscopy of long stable isotope labelled RNA.
Kremser J, Strebitzer E, Plangger R, Juen MA, Nußbaumer F, Glasner H, Breuker K, Kreutz C.*
ChemComm (2017); 53: 12938-12941. link

Synthesis and incorporation of ¹³C-labeled DNA building blocks to probe structural dynamics of DNA by NMR.
Nußbaumer F, Juen MA, Gasser C, Kremser J, Mueller T, Tollinger M, Kreutz C.*
Nucl. Acids Res. (2017); 45(15): 9178-9192. link

Phenylbenzenesulfonates and -sulfonamides as 17β-hydroxysteroid dehydrogenase type 2 inhibitors: Synthesis and SAR-analysis.
Vuorinen A, Engeli RT, Leugger S, Kreutz C, Schuster D, Odermatt A*, Matuszczak B.*
Bioorg. Med. Chem. Lett. (2017);27(13):2982-2985. link

RNA binding and chaperone activity of E. coli cold-shock protein CspA.
Rennella E, Sara T, Juen M, Wunderlich C, Imbert L, Solyom Z, Favier A, Ayala I, Weinhaeupl K, Schanda P, Konrat R, Kreutz C, Brutscher B.* 
Nucl. Acids Res. (2017);45(7):4255-4268. link

The synthesis of ¹⁵N⁷-Hoogsteen face-labeled adenosine amidite for solid phase RNA synthesis.
Neuner S, Kreutz C*, Micura R.*
Monatsh. Chem. (2017);148(1):149-155. link

A Stably Protonated Adenine Nucleotide with a Highly Shifted pK_a Value Stabilizes the Tertiary Structure of a GTP-Binding RNA Aptamer.
Wolter AC, Weickhmann AK, Nasiri AH, Hantke K, Ohlenschläger O, Wunderlich CH, Kreutz C, Duchardt-Ferner E, Wöhnert J.*
Angew. Chem. Int. Ed. Engl. (2017);56(1):401-404. link

2016

Measurement of ligand-target residence times by ¹H relaxation dispersion NMR spectroscopy.
Moschen T, Grutsch S, Juen, MA, Wunderlich CH, Kreutz C*, Tollinger M*.
J. Med. Chem. (2016);59(23):10788-10793. link

NMR resonance assignments for the tetramethylrhodamine binding RNA aptamer 3 in complex with the ligand 5-carboxy-tetramethylrhodamine.
Duchardt-Ferner E*, Juen M, Kreutz C, Wöhnert J.
Biomol. NMR Assign. (2016);11(1):29-34. link

Excited states of nucleic acids probed by proton relaxation dispersion NMR spectroscopy.
Juen MA, Wunderlich CH, Nußbaumer F, Tollinger M, Kontaxis G, Konrat R, Hansen DF*,
Kreutz C.*
Angew. Chem. Int. Ed. Engl. (2016);55(39):12008-12012. link

m¹A and m¹G disrupt A-RNA structure through the intrinsic instability of Hoogsteen base pairs.
Zhou H, Kimsey IJ, Nikolova EN, Sathyamoorthy B, Grazioli G, McSally J, Bai T, Wunderlich CH, Kreutz C, Andricioaei I*, Al-Hashimi HM.*
Nat. Struct. Mol. Biol. (2016);23:803-810. link

Pistol ribozyme adopts a pseudoknot fold facilitating site-specific in-line cleavage.
Ren A, Vusurovic N, Gebetsberger J, Gao P, Juen M, Kreutz C, Micura R*, Patel DJ.*
Nat. Chem. Biol. (2016);12:702-708. link

Chlorophyll Catabolites in Fall Leaves of the Wych Elm Tree Present a Novel Glycosylation Motif.
Scherl M, Müller T, Kreutz C, Huber RG, Zass E*, Liedl KR,* Kräutler B.*
Chemistry Eur. J. (2016);22(28):9498-9503. link

Chemo-enzymatic synthesis of site-specific isotopically labeled nucleotides for use in NMR resonance assignment, dynamics and structural characterizations.
Longhini AP, LeBlanc RM, Becette O, Salguero C, Wunderlich CH, Johnson BA, D’Souza VM, Kreutz C, Dayie TK.*
Nucl. Acids Res. (2016);44(6):e52. link

2015

Stable Isotope-Labeled RNA Phosphoramidites to Facilitate Dynamics by NMR.
Wunderlich CH, Juen MA, LeBlanc RM, Longhini AP, Dayie TK, Kreutz C.*
Methods Enzymol. 2015;565:461-494. link

A Mini-Twister Variant and Impact of Residues/Cations on the Phosphodiester Cleavage of this Ribozyme Class.
Košutić M, Neuner S, Ren A, Flür S, Wunderlich C, Mairhofer E, Vušurović N, Seikowski J, Breuker K, Höbartner C, Patel DJ*, Kreutz C*, Micura R.*
Angew. Chem. Int. Ed. Engl. (2015);127(50):15343-15348. link

NMR resonance assignments for the class II GTP binding RNA aptamer in complex with GTP.
Wolter AC, Duchardt-Ferner E, Nasiri AH, Hantke K, Wunderlich CH, Kreutz C, Wöhnert J.*
Biomol. NMR Assign. (2015);10(1):101-105. link

Hydroxymethylated Dioxobilins in Senescent Arabidopsis thaliana Leaves: Sign of a Puzzling Biosynthetic Intermezzo of Chlorophyll Breakdown.
Süssenbacher I, Kreutz C, Christ B, Hörtensteiner S, Kräutler B.*
Chem. Eur. J. (2015), 21. link

The "speedy" synthesis of atom-specific ¹⁵N imino/amido-labeled RNA.
Neuner S, Santner T, Kreutz C, Micura R.*
Chem. Eur. J. (2015), 21(33):11634-11643. link

Expanding the Scope of 2'-SCF₃ Modified RNA.
Jud L, Košutić M, Schwarz V, Hartl M, Kreutz C, Bister K, Micura R.*
Chem. Eur. J. (2015);21(29):10400-7. link

Role of a ribosomal RNA phosphate oxygen during the EF-G-triggered GTP hydrolysis.
Koch M, Flür S, Kreutz C, Ennifar E, Micura R*, Polacek N.*
Proc. Natl. Acad. Sci. USA (2015);112(20):E2561-8. link

Intermolecular 'cross-torque': the N⁴-cytosine propargyl residue is rotated to the 'CH'-edge as a result of Watson-Crick interaction.
Domingo O, Hellmuth I, Jäschke A, Kreutz C, Helm M.*
Nucl. Acids Res. (2015); 43(11):5275-5283. link

Ligand-Detected Relaxation Dispersion NMR Spectroscopy: Dynamics of preQ₁–RNA Binding.
Moschen T, Wunderlich C, Spitzer R, Levic J, Micura R, Tollinger M*, Kreutz C.*
Angew. Chem. Int. Ed. (2015); 54(2):560-563. link

2014 & before

book contributions

NMR of Large Molecules
Wunderlich C, Grutsch S, Tollinger M, Kreutz C, (2014), in ‘Handbook of Chemical and Biological Plant Analytical Methods’, edited by Kurt Hostettmann, Shilin Chen, Andrew Marston and Hermann Stuppner. Chichester, UK: John Wiley & Sons, Ltd, pp 361-378.

Investigations on fluorine-labeled ribonucleic acids by ¹⁹F-NMR spectroscopy.
Kreutz C, Micura R.
Modified Nucleotides in Biochemistry, Biotechnology and Medicine (Editor: P. Herdewijn), Wiley-VCH, (2008), 3-22.