Dr. Bruhn, Torsten

Research Topics

• Structural studies on natural products and porphyrinoids with quantum chemical methods
• prediction of optical properties of organic and organometallic molecules with a special emphasis on chiroptical properties by TDDFT or Coupled Cluster methods
• Elucidation of absolute configurations of organic molecules by a combination of experimental and quantum chemically predicted spectra (NMR, UV, ECD, IR, VCD)
• SpecDis

For examples have a look at  the publication list

Publications

58. Circularly Polarized Luminescence from Axially Chiral BODIPY DYEmers: An Experimental and Computational Study, F. Zinna, T. Bruhn, C. A. Guido, J. Ahrens, M. Bröring, L. Di Bari, G. Pescitelli, Chem. Eur. J. 2016, published online, DOI:10.1002/chem.201602684 (Hot Paper with Cover).

57. Cryptochirality in 2,2′-Coupled BODIPY DYEmers, T. Bruhn*, G. Pescitelli, F. Witterauf, J. Ahrens, M. Funk, B. Wolfram, H. Schneider, U. Radius, M. Bröring*, Eur. J. Org. Chem. 2016, 4236-4243.

56. Trangmolins A–F with an Unprecedented Structural Plasticity of the Rings A and B: New Insight into Limonoid Biosynthesis, W. Li, L. Shen, T. Bruhn, P. Pedpradab, J. Wu, G. Bringmann, Chem. Eur. J. 2016, 22, 11719–11727.

55. Good Computational Practice in the Assignment of Absolute Configurations by TDDFT Calculations of ECD Spectra, G. Pescitelli*, T. Bruhn*, Chirality 2016, published online, DOI:10.1002/chir.22600 (Editors Choice Article).

54. Axial, Helical, and Planar Chirality in Directly Linked Basket-Handle Porphyrin Arrays, A. C. Gehrold, T. Bruhn*, G. Bringmann*, J. Org. Chem. 2016,  81, 1075-1088..

53. Monomeric Chiral and Achiral Basket-Handle Porphyrins: Synthesis, Structural Features, and Arrested Tautomerism; A. C. Gehrold, T. Bruhn*, H. Schneider, U. Radius, G. Bringmann*, J. Org. Chem. 2015, 80, 12359–12378.

52. Singlet oxygen oxidation products of biliverdin IXα dimethyl ester; S. J. Dorazio, S. Halepas, T. Bruhn, K. M. Fleming, M. Zeller, C. Brückner, Bioorg. Med. Chem. 2015, 23, 7671-7675.

51. Stereoisomeric Composition of Natural Myrtucommulone A; M. Hans, M. Charpentier, V. Huch, J. Jauch, T. Bruhn, G. Bringmann, J. Nat. Prod. 2015, 78, 2381-2389.

50. The role of magnetic-electric coupling in exciton-coupled ECD spectra. The case of bis-phenanthrenes, S. Jurinovich, C. A. Guido, T. Bruhn, G. Pescitelli, B. Mennucci, Chem. Commun. 2015, 51, 10498-10501.

49. Antiviral Limonoids Including Khayanolides from the Trang Mangrove Plant Xylocarpus moluccensis, W. Li, Z. Jiang, L. Shen, P. Pedpradab, T. Bruhn, J. Wu, G. Bringmann, J. Nat. Prod. 2015, 78, 1570–1578.

48. Indaphyrins and Indachlorins: Optical and Chiroptical Properties of a Family of Helimeric Porphyrinoids, D. C. G. Götz, A. C. Gehrold, S. J. Dorazio, P. Daddario, L. Samankumara, G. Bringmann, C. Brückner*, T. Bruhn*, Eur. J. Org. Chem. 2015, 3913-3922.

47. Origin of the Regioselective Reduction of Chlorins, T. Bruhn*, C. Brückner*, J. Org. Chem. 2015, 80, 4861–4868 (Cover Article).

46. Chiral and Achiral Basket-Handle Porphyrins: Short Synthesis and Stereostructures of These Versatile Building Blocks; A. C. Gehrold, T. Bruhn, H. Schneider, U. Radius, G. Bringmann, Org. Lett. 2015, 17, 210-213.

45. The Origin of the Absorption Spectra of Porphyrin N- and Dithiaporphyrin S-oxides in their Neutral and Protonated states; T. Bruhn*, C. Brückner, Phys. Chem. Chem. Phys. 2015, 17, 3560-3569.

44. Axially Chiral BODIPY DYEmers: An Apparent Exception to the Exciton Chirality Rule; T. Bruhn*, G. Pescitelli*, S. Jurinovich, A. Schaumlöffel, F. Witterauf, J. Ahrens, M. Bröring, G. Bringmann*, Angew. Chem. Int. Ed. 2014, 53, 14592-14595; Axial-chirale BODIPY-DYEmers: eine offensichtliche Ausnahme für die Exciton-Chiralitäts-Methode; T. Bruhn*, G. Pescitelli*, S. Jurinovich, A. Schaumlöffel, F. Witterauf, J. Ahrens, M. Bröring, G. Bringmann*, Angew. Chem. 2014, 126, 14821-14824.

43. A photoinduced mixed-valence state in an organic bis-triarylamine mixed-valence compound with an iridium-metal-bridge, C. Lambert*, R. Wagener, J. H. Klein, G. Grelaud, M. Moos, A. Schmiedel, M. Holzapfel, T. Bruhn, Chem. Commun. 2014, 50, 11350-11353.

42. C,C- and N,C-Coupled Dimers of 2-Aminotetraphenylporphyrins: Regiocontrolled Synthesis, Spectroscopic Properties, and Quantum-Chemical Calculations, T. Bruhn, F. Witterauf, D. C. G. Götz, C. T. Grimmer, M. Würtemberger, U. Radius, G. Bringmann*, Chem. Eur. J. 2014, 20, 3998-4006.

41. Nature’s Lab for Derivatization: New and Revised Structures of a Variety of Streptophenazines Produced by a Sponge-Derived Streptomyces Strain, A. Kunz, A. Labes, J. Wiese, T. Bruhn, G. Bringmann, J. Imhoff*, Mar. Drugs 2014, 12, 1699-1714.

40. Thaixylomolins A–C: Limonoids Featuring Two New Motifs from the Thai Xylocarpus moluccensis, J. Li, M.-Y. Li, T. Bruhn, F. Z. Katele, Q. Xiao, P. Pedpradab, J. Wu, G. Bringmann, Org. Lett. 2013, 15, 3682–3685.

39. New bhimamycins from Streptomyces sp. AK 671, P. Jetter, C. Steinert, M. Knauer, G. Zhang, T. Bruhn, J. Wiese, J. F. Imhoff, H.-P. Fiedler, G. Bringmann, J. Antibiot. 2013, 66, 719-726.

38. Regiodivergent N-C and N-N Aryl Coupling Reactions of Indoloterpenes and Cycloether Formation Mediated by a Single Bacterial Flavoenzyme, M. Baunach, L. Ding, T. Bruhn, G. Bringmann, C. Hertweck*, Angew. Chem. Int. Ed. 2013, 34, 9040-9043; Regiodivergent N-C and N-N Aryl Coupling Reactions of Indoloterpenes and Cycloether Formation Mediated by a Single Bacterial Flavoenzyme, M. Baunach, L. Ding, T. Bruhn, G. Bringmann, C. Hertweck*, Angew. Chem. 2013, 125, 9210-9213.

37. SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra, T. Bruhn*, A. Schaumlöffel, Y. Hemberger, G. Bringmann*, Chirality 2013, 25, 243–249.

36. Helicusin E, Isochromophilone X and Isochromophilone XI: new chloroazaphilones produced by the fungus Bartalinia robillardoides strain LF550, N. Jansen, B. Ohlendorf, A. Erhard, T. Bruhn, G. Bringmann, J.F. Imhoff, Marine Drugs 2013, 11, 800-816.

35. Andhraxylocarpins A-E: Structurally Intriguing Limonoids from Mangroves, Xylocarpus granatum and Xylocarpus moluccensis, Collected in the Estuaries of Andhra Pradesh, J. Li, M.-Y. Li, T. Bruhn, D. C.G. Götz, Q. Xiao, T. Satyanandamurty, J. Wu, G. Bringmann, Chem. Eur. J. 2012, 18, 14342–14351.

34. Ultrafast exciton dynamics after Soret- or Q-band excitation of a directly β,β′-linked bisporphyrin, M. Kullmann, A. Hipke, P. Nuernberger, T. Bruhn, D. C. G. Götz, M. Sekita, D. M. Guldi, G. Bringmann, T. Brixner, Phys. Chem. Chem. Phys. 2012, 14, 8038-8050.

33. The Online Stereochemical Analysis of Chiral Compounds by HPLC-ECD Coupling in Combination with Quantum-Chemical Calculations, G. Bringmann, D. Götz, T. Bruhn, in Comprehensive Chiroptical Spectroscopy, Vol. 2 (Eds.: N. Berova, R. W. Woody, P. Polavarapu, K. Nakanishi), John Wiley & Sons, 2012, pp. 355-386.

32. (+)-Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics, S. Loesgen, T. Bruhn, K. Meindl, I. Dix, B. Schulz, A. Zeeck, G. Bringmann, Eur. J. Org. Chem. 2011, 5156–5162.

31. Helimeric Porphyrinoids: Stereostructure and Chiral Resolution of meso-Tetraarylmorpholinochlorins, C. Brückner, D. C. G. Götz, S. P. Fox, C. Ryppa, J. R. McCarthy, T. Bruhn, J. Akhigbe, S. Banerjee, P. Daddario, H. W. Daniell, M. Zeller, R. W. Boyle, G. Bringmann, J. Am. Chem. Soc. 2011, 133, 8740–8752.

30. Chloropupukeanolides C–E: Cytotoxic Pupukeanane Chlorides with a Spiroketal Skeleton from Pestalotiopsis fici, L. Liu, T. Bruhn, L. Guo, D. C. G. Götz, R. Brun, A. Stich, Y. Che, G. Bringmann, Chem. Eur. J. 2011, 17, 2604-2613 (Cover Picture).

29. Aspergiolides C and D: Spirocyclic Aromatic Polyketides with Potent Protein Kinase c-Met Inhibitory Effects, L. Du, J. Ai, D. Li, T. Zhu, Y. Wang, M. Knauer, T. Bruhn, H. Liu,  M. Geng, Q. Gu, G. Bringmann, Chem. Eur. J. 2011, 17, 1319–1326.

28. Catechin Derivatives from Parapiptadenia rigida with in Vitro Wound-Healing Properties, C. A. Schmidt, R. Murillo, T. Bruhn, G. Bringmann, M. Goettert, B. Heinzmann, V. Brecht, S. A. Laufer, I. Merfort, J. Nat. Prod. 2010, 73, 2035–2041.

27. Sorbifuranones A-C, Sorbicillinoid Metabolites From Penicillium Strains Isolated From Mediterranean Sponges, G. Bringmann, G. Lang, T. Bruhn, K. Schäffler, S. Steffens, R. Schmaljohann, J. Wiese, J. F. Imhoff, Tetrahedron 2010, 66, 9894-9901.

26. Baculiferins A–O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera, G. Fan, Z. Li,S. Shen, Y. Zeng, Y. Yang, M. Xu, T. Bruhn, H. Bruhn, J. Morschhäuser, G. Bringmann, W. Lin, Bioorg. Med. Chem. 2010, 18, 5466–5474.

25. Shuangancistrotectorines A-E, Dimeric Naphthylisoquinoline Alkaloids with Three Chiral Biaryl Axes from the Chinese Plant Ancistrocladus tectorius, M. Xu, T. Bruhn, B. Hertlein, R. Brun, A. Stich, J. Wu, G. Bringmann, Chem. Eur. J. 2010, 16, 4206-4216 (Cover picture).

24. Synthesis and Stereochemical Characterization of Highly Unsymmetric ß,meso-Linked Porphyrin Arrays, D.C.G. Götz, T. Bruhn, O. Senge, G. Bringmann, J. Org. Chem. 2009, 74, 8005–8020. (Featured Article and Cover Art).

23. Quantum Chemical CD Calculations of Dioncophylline A in the Solid State, G. Bringmann, K. Maksimenka, T. Bruhn, M. Reichert, T. Harada, R. Kuroda, Tetrahedron 2009, 65, 5720-5728.

22. The Assignment of Absolute Stereostructures by Quantum Chemical Circular Dichroism Calculations, G. Bringmann, T. Bruhn, K. Maksimenka, Y. Hemberger, Eur. J. Org. Chem. 2009, 2717 - 2727.

21. Synthesis and Helicate Formation of a New Family of BINOL-Based Bis(bipyridine) Ligands, J. Bunzen, T. Bruhn, G. Bringmann, A. Lützen, J. Am. Chem. Soc. 2009, 131, 3621–3630.

20. Cleavage of Four Carbon-Carbon Bonds during Biosynthesis of the Griseorhodin A Spiroketal Pharmacophore, Z. Yunt, K. Reinhardt, A. Li, M. Engeser, H.-M. Dahse, M. Gütschow, T. Bruhn, G. Bringmann, J. Piel, J. Am. Chem. Soc. 2009, 131, 2297-2305.

19. Axially Chiral ß,ß’-Bisporphyrins: Synthesis and Configurational Stability Tuned by the Central Metals, G. Bringmann, D.C.G. Götz, T.A.M. Gulder, T.H. Gehrke, T. Bruhn, T, Kupfer, K. Radacki, H. Braunschweig, A. Heckmann, C. Lambert, J. Am. Chem. Soc. 2008, 130, 17812–17825.

18. Reaction of Iminopropadienones with Amines: Mechanistic Explanations of Zwitterionic Intermediate, Ketene and Ketenimine Formation, R. Koch, J. Finnerty, T. Bruhn, F. Borget, C. Wentrup, J. Phys. Chem. A 2008, 112, 8999-9004.

17. Antitumoral Dioncoquinones A and B and ancistroquinones B-F from cell cultures of Triphyophyllum peltatum and Ancistrocladus abbreviatus, G. Bringmann, S. Rüdenauer, A. Irmer, T. Bruhn, R. Brun, T. Heimberger, T. Stühmer, R. Bargou, M. Chatterjee, Phytochemistry 2008, 69, 2501-2509.

16. Theoretical study on the nonlinear optical properties of phenylenes and influencing factors, R. Koch, J. J. Finnerty, T. Bruhn, J. Phys Org. Chem. 2008, 21, 954-962.

15. Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4’-O-demethylancistrobertsonine C by asymmetric Suzuki cross coupling reaction, G. Bringmann, S. Rüdenauer, T. Bruhn, L. Benson, Tetrahedron 2008, 64, 5563-5568.

14. Synthesis, resolution, and Absolute Configuration of Difunctionalized Tröger´s Base Derivatives, U. Kiehne, T. Bruhn, G. Schnakenburg, R. Fröhlich, G. Bringmann, A. Lützen, Chem. Eur. J. 2008, 14, 4246-4255.

13. Xylogranatins F-R: Antifeedants from the Chinese Mangrove, Xylocarpus granatum, Suggesting a New Biogenetic Pathway to Tetranortriterpenoids, J. Wu, S. Zhang, Q. Xiao, H. Ding, T. Bruhn, G. Bringmann,  Chem. Eur. J. 2008, 14, 1129-1144.

12. Synthesis and Pharmacological Evaluation of Photoactivatable Antiplasmodial Naphtylisoquinoloine Alkaloids for Application in Photoaffinity Labeling, G. Bringmann, C. Gampe, Y. Reichert, T. Bruhn, J. H. Faber, M. Mykina, M. Reichert, M. Leippe, R. Brun, C. Gelhaus,  J. Med. Chem. 2007, 50, 6104-6115.

11. The absolute axial configurations of knipholone and knipholone anthrone by TDDFT and DFT/MRCI CD calculations: a revision, G. Bringmann, K. Maksimenka, J. Mutanyatta-Comar, M. Knauer, T. Bruhn, Tetrahedron 2007, 63, 9810-9824.

10. Shearinines D-K, new indole triterpenoids from an endophytic Penicillium sp. (strain HKI0459) with blocking activity on large conductance calcium-activated potassium channels, M. Xu, G. Gessner, I. Groth, C. Lange, A. Christner, T. Bruhn, Z. Deng, X. Li, S. H. Heinemann, S. Grabley, G. Bringmann, I. Sattler, W. Lin, Tetrahedron 2007, 63, 435-444.

9. Theoretical ⁴⁹Ti NMR chemical shifts. R. Koch, T. Bruhn, J. Mol. Model. 2006, 12, 723 – 729.

8. Theoretical Group 14 Chemistry. Part 4. Cyclotriplumbanes: Relativistic and Substituent Effects. R. Koch, T. Bruhn, M. Weidenbruch, J. Chem. Theo. Comp. 2005, 1, 1298 – 1303.

7. Investigation of the Structure of Neodymium-Di-(2-Ethylhexyl) Phosphoric Acid Combinations Using Electrospray Ionization and Matrix-Assisted Laser Desorption Ionization Mass Spectrometry and Nuclear Magnetic Resonance Spectroscopy, C. Scharf, A. Ditze, K. Schwerdtfeger, S. Fürmeier, T. Bruhn, D. E. Kaufmann, J. C. Namyslo, Met. Mat. Trans. B 2005, 36, 429-436.

6. Theoretical Group 14 chemistry. Part 3. A DFT Study of Ge₄R₆, R. Koch, T. Bruhn, M. Weidenbruch, J. Mol. Struct. (THEOCHEM) 2005, 714, 109-115 .

5. Iminopropadienones R-N=C=C=C=O and carbon suboxide, C₃O₂. Theoretical and experimental ¹³C NMR spectra, R. Koch, T. Bruhn, R. N. Veedu, C. Wentrup, J. Mol. Struct. (THEOCHEM) 2004, 686, 31–36.

4. Theoretical Group 14 chemistry. Part 2. Si₄R₆ – a theoretical approach, R. Koch, T. Bruhn, M. Weidenbruch, J. Mol. Struct. (THEOCHEM) 2004, 680, 91-97.

3. Silylene and Germylene Additions to 1,3-Diynes: Bis(silacyclopropenes) vs. Germaethenes Formation, a DFT Study, R. Koch, T. Bruhn, M. Weidenbruch, Organometallics 2004, 23, 1570-1575.

2. Untersuchung von reaktiven Zwischenstufen bei chemischen Reaktionen in Lösung mit Elektrospray-Ionisations-Massenspektrometrie: Radikalkettenreaktionen, J. Griep-Raming, S. Meyer, T. Bruhn, J. O. Metzger, Angew. Chem. 2002, 114, 2863 – 2866; Investigation of Reactive Intermediates of Chemical Reactions in Solution by Electrospray Ionization Mass Spectrometry: Radical Chain Reactions, J. Griep-Raming, S. Meyer, T. Bruhn, J. O. Metzger, Angew. Chem. Int. Ed. 2002, 41, 2738 - 2742.

1. Synthesis and recognition behaviour of allosteric hemicarcerands, A. Lützen, O. Haß, T. Bruhn, Tetrahedron Letters 2002, 43, 1807 - 1811.

PhD Thesis

Reaktive organische und anorganische Systeme mit Gruppe 14 Elementen:eine computerchemische Analyse

Written at the Institute for Pure and Applied Chemistry, University of Oldenburg, in the working group of Dr. Rainer Koch.

 

Diploma Thesis

Untersuchungen an Carbeniumionen mittels ESI-Massenspektrometrie

Written at the Institute for Pure and Applied Chemistry, University of Oldenburg, in the working group of Prof. Dr. Jürgen O. Metzger.

 

Lectures

T. Bruhn, A. Schaumlöffel, Chiroptische Spektroskopie in der Naturstoffchemie: HPLC-CD, Festkörper-CD und ORD; October 2009, Naturstofftreffen, Leibniz-Institut für Pflanzenbiochemie, Halle, Germany.

Structural Elucidation of Chiral Natural Products by Quantum Chemical Calculations; October 2008, "Naturstofftreffen", Würzburg, Germany.

Structural Elucidation of Chiral Natural Products by Quantum Chemical Calculations ; July 2008, "Tübinger Gespräche", Blaubeuren, Germany.

Poster

An Apparent Exception to the Exciton Chirality Method - Recent Developments in the Determination of the Absolute Configuration using ECD Spectra, T. Bruhn, G. Pescitelli, S. Jurinovich, A. Schaumlöffel, G. Bringmann, 27. Irseer Naturstofftage, February 2015, Irsee, Germany.

Synthesis and Stereostructures of Axially Chiral Dimeric Basket-handle Porphyrins, A. Gehrold, T. Bruhn, F. Witterauf, H. Schneider, U. Radius, G. Bringmann, 8th International Conference on Porphyrins and  Phthalocyanines 2014, Istanbul, Turkey.

Regioselective C,C- or C,N-coupling of 2-Amino-Tetraphenylporphyrins, F. Witterauf, T. Bruhn, C. T. Grimmer, D. C. G. Götz, M. Würtemberger, U. Radius, G. Bringmann, 8th International Conference on Porphyrins and  Phthalocyanines 2014, Istanbul, Turkey.

The Online Assignment of Absolute Stereostructures: HPLC-CD in Combination with Quantum Chemical CD Calculations; D. C. G. Götz, T. Bruhn, Y. Hemberger, T. Gulder, T. A. M. Gulder, M.Knauer, G. Bringmann;  21. Irseer Naturstofftage, February 2009, Irsee, Germany.

Ancistrocladus tectorius: A Rich Source of Novel-Type Naphthylisoquinoline Alkaloids - Quinoid, Pentacyclic, N,C-Coupled, Dimeric!, B. Hertlein, Y. Hemberger, M. Xu, T. Bruhn, G.Bringmann, ChemSyStM 2008, Würzburg, Germany.

Absolute Configuration Online, Right from the Peak in the Chromatogram: HPLC-CD in Combination with Quantum Chemical CD Calculations, Y. Hemberger, T. Bruhn, T. A. M. Gulder, T. Gulder, G. Bringmann, ChemSyStM 2007, Würzburg, Germany.

Theoretical Group 14 Chemistry, R. Koch, T. Bruhn, M. Weidenbruch, JCF Frühjahrssymposium 2005, Berlin, Germany.

Quantummechanical study of homonuclear lead rings, R. Koch, T. Bruhn, M. Weidenbruch, Tag der Chemie 2004, Oldenburg, Germany.

The Addition of Silylenes and Germylens to Diacetylenes - A DFT Study, R. Koch, T. Bruhn, M. Weidenbruch, 17. Darmstädter Molecular Modelling Workshop 2003, Erlangen, Germany.

The Addition of Silylenes and Germylens to Diacetylenes - A DFT Study, R. Koch, T. Bruhn, M. Weidenbruch, Tag der Chemie 2003, Oldenburg, Germany.

Untersuchung der Dissoziation von Kohlenstoff-Heteroatom-Bindungen in Lösung: Nachweis der Carbokationen und der Anionen durch ESI-MS, T. Bruhn, J. O. Metzger, Diskussionstagung der DGMS 2002, Heidelberg, Germany.

Auf dem Weg zum direkten Nachweis von Carbeniumionen in Lösung, T. Bruhn, J. O. Metzger, Tag der Chemie 2001, Oldenburg, Germany.