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Dirk Trauner: CIPSM-Professorship for chemical biology and chemical genetics
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Dirk Trauner was born and grew up in Linz, Austria. After studying biology and then biochemistry at the University of Vienna, he joined Professor Johann Mulzer's group at the Freie Universität Berlin to pursue natural product synthesis. In the late 1990s, he was a postdoctoral fellow with Samuel J. Danishefsky at the Memorial Sloan-Kettering Cancer Center in New York City. Dirk was an associate professor of chemistry at the University of California at Berkeley from 2000-8. We are happy, that Dirk will join CIPSM at the Department of Chemistry and Biochemistry of the Ludwig-Maximilians-Universität München (LMU) in August 2008.
Research interests
Organic and Bioorganic Chemistry — Total synthesis of bioactive natural products, synthetic methodology, molecular machines, and chemical neurobiology
Our research centers on the total synthesis of complex natural products and rationally designed molecular probes and their application to biological problems, especially in neuroscience. A large part of our research program is dedicated to the synthesis and biological evaluation of natural products - that is biologically active metabolites with relatively low molecular weights. We are convinced that the majority of natural products have not yet been found and that a wealth of interesting chemistry and biology awaits discovery. As synthetic organic chemists, we are intrigued by the structural beauty and functional sophistication of natural products. Through the power of total synthesis, we gain insight into their structure/activity relationships and biosynthetic origin. In addition, the total synthesis of complex natural products provides an ideal platform for the invention or discovery of new synthetic methodology or the validation of modern reactions in a complex environment.
Along with our studies on natural products, we are concerned with the chemical biology of neural systems. Neuroscience is indeed one of the most exciting scientific frontiers of our time. As its molecular foundation becomes established, this field is currently undergoing the same transformation that has propelled genetics to the forefront of science and has ultimately led to the elucidation of the human genome. Until recently, progress in the neurosciences has been hampered by a lack of structural understanding of the basic components that underlie the function of excitable cells: the ionotropic receptors, i.e. ion channels, and the metabotropic receptors, i.e. G-protein coupled receptors. With the emergence of the first X-ray crystal structures of these proteins, this situation has changed dramatically and neurobiology is bound to mature into a truly molecular science. We believe that the time has come for organic chemists, who have a keen understanding of structure and mechanism and the ability to synthesize complex molecules, to make an impact on this field. Our current focus lies on the functional reengineering of ion channels by attaching synthetic switches that respond to a diverse array of input signals. These manipulated ion channels can be inserted into excitable cells, e.g. neurons, and can render them sensitive to new stimuli, e.g. light.
Contact
Prof. Dr. Dirk Trauner
Department of Chemistry
University of California at Berkeley
602 Latimer
Phone: + (510)643-5507
Email: trauner@berkeley.edu
Publications
78. "Biomimetic Synthesis of the Shimalactones." Sofiyev, V.; Navarro, G.; Trauner, D.Org. Lett. 2007, 9, ASAP.
77. "Regulating Enzymatic Activity with a Photoswitchable Affinity Label." Harvey, J.; Trauner, D. Chem. Biochem. 2007, 9, ASAP.
76. "All Optical Interface for Parallel, Remote, and Spatiotemporal Control of Neuronal Activity." Wang, S.; Szobota, S.; Wang, Y.; Volgraf, M.; Liu, Z.; Sun, C.; Trauner, D.; Isacoff, E. Y.; Zhang, X. Nano Lett. 2007, 7, ASAP.
75. "Reversible Photomechanical Switching of Individual Engineered Molecules at a Metallic Surface." Comstock, M. J.; Levy, N.; Kirakosian, A.;Cho, J.; Lauterwasser, F.; Harvey, J. H.; Strubbe, D. A.;Fréchet, J. M. J.; Trauner, D.; Louie, S. G.; Crommie, M. F. Phys. Rev. Lett. 2007, 99, 038301.
74. "Total Synthesis of (-)-Archazolid B." Roethle, P. A.; Chen, I. T.; Trauner, D. J. Am. Chem. Soc. 2007, 129, 8960.
73. "Mechanisms of photoswitch conjugation and light activation of an ionotropic glutamate receptor." Gorostiza, P.; Volgraf, M.; Numano,R.; Szobota, S.; Trauner, D.; Isacoff, E. Y.Proc. Natl. Acad. Sci. 2007, 104, 10865.
72. "Total Synthesis of Smenochromene B Through Ring Contraction." Rosa, C.P.; Kienzler, M.; Olson, B.S.; Liang, G.; Trauner, D. Tetrahedron 2007, 63, 6529.
71. "Remote Control of Neuronal Activity With a Light-Gated Glutamate Receptor." Szobota, S.; Gorostiza, P.; Del Bene, F.; Wyart, C.; Fortin, D. L.; Kolstad, K. D.; Tulyathan, O.; Volgraf, M.; Numano, R.; Aaron, H. L.; Scott, E. K.; Kramer, R. H.; Flannery, J.; Baier, H.; Trauner, D.; Isacoff, E. Neuron 2007, 54, 535.
70. "Functionalized Azobenzenes Through Cross-Coupling with Organotrifluoroborates" Harvey, J. H.; Bulter, B. K.; Trauner, D. Tetrahedron Lett. 2007, 48, 1661.
69. "Concise Synthesis of the Bacterial DNA Primase Inhibitor (+)-Sch 642305" Wilson, E. M.; Trauner, D. Org. Lett. 2007, 9, 1327.
68. "Reversibly Caged Glutamate: A Photochromic Agonist of Ionotropic Glutamate Receptors" Volgraf, M.; Gorostiza, P.; Szobota,S.; Helix, M. R.; Isacoff, E. Y.; Trauner, D. J. Am. Chem. Soc. 2007, 129, 260.
67. "Total Synthesis of (-)-Heptemerone B and (-)-Guanacastepene E" Miller, A. K.; Hughes, C. C.; Kennedy-Smith, J. J.; Gradl, S. N.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 17057.
66. "Engineering Light-Gated Ion Channels" Banghart, M. R.; Volgraf, M.; Trauner, D. Biochemistry 2006, 45, 15129.
65. "Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (-)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B " Roethle, P. A.; Hernandez, P. T.; Trauner, D. Org. Lett. 2006, 8, 5901.
64. "Development of a Friedel-Crafts Triflation" Grundl, M. A.; Kaster, A.; Beaulieu, E. D.; Trauner, D. Org. Lett. 2006, 8, 5429.
63. "Photochemical Origin of the Immunosuppressive SNF4435C/D and Formation of Orinocin through Polyene Splicing" Müller, M.; Kusebauch, B.; Liang, G.; Beaudry, C. M.; Trauner, D.; Hertweck, C. Angew. Chem. Int. Ed. 2006, 46, 7835.
62. "Mapping the Chemistry of Highly Unsaturated Pyrone Polyketides" Miller, A.K.; Trauner, D. Synlett. 2006, 14, 2295.
61. "Light-Induced Depolarization of Neurons Using a Modified Shaker K Channel and a Molecular Photoswitch" Chambers, J. J.; Banghart, M. R.; Trauner, D.; Kramer, R. H. J. Neurophysiol. 2006, 96 2792.
60. "Synthesis of Taiwaniaquinoids via Nazarov Triflation" Liang, G.; Xu, Y.; Seiple, I.B.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 11022.
59. "An Expedient Synthesis of (±)-Bipinnatin J." Roethle, P. A.; Trauner, D. Org. Lett. 2006, 8, 345.
58. "Synthetic Studies Toward the Haouamines." Grundl, M. A.; Trauner, D. Org. Lett. 2006, 8, 23.
57. "Allosteric Control of an Ionotropic Glutamate Receptor with an Optical Switch." Volgraf, M.; Gorostiza, P.; Numano, R.; Kramer, R. H.; Isacoff, E.; Trauner, D. Nature Chem. Bio. 2006, 1, 47. Featured in "Science"
56. "Pericyclic Reactions of Prenylated Naphthoquinones: Biomimetic Synthesis of Mollugin and Microphyllaquinone." Lumb, J. P.; Trauner, D. Org. Lett. 2005, 7, 5865.
55. "Photochemical Tools for Remote-Control of Ion Channels in Excitable Cells." Kramer, R. H.; Chambers, J. J.; Trauner, D. Nature Chem. Bio. 2005, 1, 360.
54. "Biosynthetic and Biomimetic Electrocyclizations." Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757.
53. "Concise Synthesis of (±)-Rhazinilam through Direct Coupling." Bowie, A. L., Jr.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207.
52. "Photosensitized Conversion of 9,10-Deoxytridachione to Photodeoxytridachione." Zuidema, D. R.; Miller, A. K.; Trauner, D.; Jones, P. B. Org. Lett. 2005, 7, 4959.
51. "Total Synthesis of (-)-SNF4435 C and (+)-SNF4435 D." Beaudry, C. M.; Trauner, D. Org. Lett. 2005, 7, 4475.
50. "A Glimpse at the Grail." Trauner, D. Nature Chem. Bio. 2005, 1, 189.
49. "The Meirwein-Eschenmoser-Claisen Rearrangement." Gradl, S. N.; Trauner, D. In Claisen Rearrangements, Hiersemann, M.; Nubbemeyer, U., Eds; Weinheim: Wiley-VCH 2005, Chapter 7.
48. "Infrared Hole Burning and Conformational Change in a Borane-Ammonia Complex." Endicott, C. A.; Strauss, H. L.; Hughes, C. C.; Trauner, D. J. Phys Chem. A 2005, 109, 7714.
47. "An Electrochemical Approach to the Guanacastepenes." Hughes, C. C.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 3425.
46. "Mining the Tetraene Manifold: Total Synthesis of Complex Pyrones from Placobranchus ocellatus." Miller, A. K.; Trauner, D. Angew. Chem., Int. Ed. 2005, 44, 4602.
45. "Biomimetic Synthesis of Elysiapyrones A and B." Barbarow, J. E.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 2901.
44. "Stereoselective Syntheses of the Bioactive Polypropionates Aureothin, N-Acetylaureothamine, and Aureonitrile." Liang, G.; Seiple, I. B.; Trauner, D. Org. Lett. 2005, 7, 2837.
43. "Rational Design of a Chiral Palladium(0) Olefin Complex of Unprecedented Stability." Grundl, M. A.; Kennedy-Smith, J. J.; Trauner, D. Organometallics 2005, 24, 2831.
42. "Biomimetic Synthesis of Antimalarial Naphthoquinones." Malerich, J. P.; Maimone, T. J.; Elliott, G. I.; Trauner, D. J. Am. Chem. Soc. 2005, 127, 6276.
41. "Dienophile Twisting Causes Rate Enhancements in Intramolecular Diels-Alder Cycloadditions: A DFT Study." Khuong, K. S.; Beaudry, C.; Trauner, D.; Houk, K. N. J. Am. Chem. Soc. 2005, 127, 3688.
40. "Biomimetic Synthesis and Structure Elucidation of Rubicordifolin, a Cytotoxic Natural Product from Rubia cordifolia." Lumb, J. P.; Trauner, D. J. Am. Chem. Soc. 2005, 127, 2870.
39. "Stereoselective Synthesis of the Placidenes and Cyercene A." Liang, G.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 819.
38. "Concise Synthesis of (±)-Smenochromene D (Likonide B)." Olson, B. S.; Trauner D, Synlett 2005, 700.
37. "Biomimetic Synthesis of Natural Products Isolated from Bignoniaceae." Malerich, J. P.; Trauner, D. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed.; Elsevier: Amsterdam, 2004; Vol. 5. pp 417-436.
36. "Light-Activated Ion Channels for Remote Control of Neuronal Firing." Banghart, M. R.; Borges, K.; Isacoff, E. Y.; Trauner, D.; Kramer R. H. Nature Neuroscience 2004, 7, 1381. Featured in Science
35. "Palladium-Catalyzed Couplings to Nucleophilic Heteroarenes: The Total Synthesis of (-)-Frondosin B." Hughes, C. C.; Trauner, D. Tetrahedron 2004, 60, 9675.
34. "Enantioselective Nazarov Reactions through Catalytic Asymmetric Proton Transfer." Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544.
33. "The Total Synthesis of (-)-Crispatene." Miller, A. K.; Byun, D. H.; Beaudry, C. M.; Trauner, D. Proc. Natl. Acad. Sci. 2004, 101, 12019.
32. "Metabolic Modulation of Potassium Channels." Trauner, D.; Kramer, R. H. Science STKE 2004, 233, pe20.
31. "Efficient Nazarov Cyclizations of 2-Alkoxy-1,4-pentadien-3-ones." Liang, G.; Gradl, S. N.; Trauner, D. Org. Lett. 2003, 5, 4931.
30. "Potassium Channels: Symmetric, Selective, Sensitive." Trauner, D. Angew. Chem., Int. Ed. 2003, 42, 5671.
29. "Direct Catalytic Asymmetric Amination of Aldehydes: Synthesis of Evans Oxazolidinones and α-Amino Acids." Hughes, C. C.; Trauner, D. Chemtracts 2003, 16, 511.
28. "Development of Novel Lewis Acid Catalyzed Cycloisomerizations: Synthesis of Bicyclo[3.1.0]hexenes and Cyclopentenones." Miller, A. K.; Banghart, M. R.; Beaudry, C. M.; Suh, J. M.; Trauner, D. Tetrahedron 2003, 59, 8919.
27. "Synthetic Studies toward the Guanacastepenes." Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113.
26. "Protein Surface Recognition by Rational Design: Nanomolar Ligands for Potassium Channels." Gradl, S.; Felix, J. P.; Isacoff, E. Y.; Garcia, M. L.; Trauner, D. J. Am. Chem. Soc. 2003, 125, 12668.
25. "Reductive Cyclization of β-Hydroxy Nitriles: A New Synthesis of Glycoxylamines." Dorsey, A. D.; Barbarow, J. E.; Trauner, D. Org. Lett. 2003, 5, 3237.
24. "Biomimetic Synthesis of (±)-Pinnatal and (±)-Sterekunthal A." Malerich, J. P.; Trauner, D. J. Am. Chem. Soc. 2003, 125, 9554.
23. "Intramolecular Diels-Alder Reactions of 5-Vinyl-1,3-Cyclohexadienes." Ng, S. M.; Beaudry, C. M.; Trauner, D. Org. Lett. 2003, 5, 1701.
22. "Total Synthesis of (±)-Photodeoxytridachione through a Lewis Acid Catalyzed Cyclization." Miller, A. K.; Trauner, D. Angew. Chem., Int. Ed. 2003, 42, 549.
21. "Enzymatic Desymmetrization of a Centrosymmetric Diacetate." Böhm, C.; Austin, W. F.; Trauner, D. Tetrahedron: Asymmetry 2003, 14, 71.
20. "The Total Synthesis of (-)-Amathaspiramide F." Hughes, C. C.; Trauner, D. Angew. Chem., Int. Ed. 2002, 41, 4556.
19. "Boron-Ammonia Complexes Stabilized by Hydrogen Bonding." Hughes, C. C.; Scharn, D.; Mulzer, J.; Trauner, D. Org. Lett. 2002, 4, 4109.
18. "Synthetic Studies Toward SNF4435 C and SNF4435 D." Beaudry, C. M.; Trauner, D. Org. Lett. 2002, 4, 2221.
17. "Concise Total Synthesis of (-)-Frondosin B Using a Novel Palladium Catalyzed Cyclization." Hughes, C. C.; Trauner, D. Angew. Chem., Int. Ed. 2002, 41, 1569.
16. "A Practical Variant of the Claisen-Eschenmoser Rearrangement: Synthesis of Unsaturated Morpholine Amides." Gradl, S. N.; Kennedy-Smith, J. J.; Kim, J.; Trauner, D. Synlett 2002, 3, 411.
15. "The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study and Applications in Natural Product Synthesis." Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
14. "Concise Stereoselective Routes to Advanced Intermediates Related to Natural and Unnatural Pinnaic Acid." Carson, M. W.; Kim, G.; Hentemann, M. F.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4450.
13. "On the Conformations of Halichlorine and the Pinnaic Acids: Nitrogen Inversion as a Possible Determinant of Biological Profile." Trauner, D.; Danishefsky, S. J. Helv. Chim. Acta 2000, 83, 2344.
12. "Synthesis of Immunomodulatory Marine Natural Products." Danishefsky, S. J.; Inoue, M.; Trauner, D. in "The Role of Natural Products in Drug Discovery," Ernst Schering Research Foundation (ESRF) Workshop 32, pp. 1-24, Heidelberg, New York: Springer 2000.
11. "Morphine Synthesis and Biosynthesis--an Update." Novak, B. H.; Hudlicky, T.; Reed, J. W.; Mulzer, J.; Trauner, D. Curr. Org. Chem. 2000, 4, 343.
10. "Total Synthesis of (+)-Halichlorine, an Inhibitor of VCAM-1 Expression." Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542.
9. "Studies Toward the Total Synthesis of Halichlorine: Asymmetric Synthesis of the Spiroqinolizidine Subunit." Trauner, D.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 6513.
8. "Insight into the Mechanism of the Saegusa Oxidation: Isolation of a Novel Palladium(0) Tetraolefin Complex." Porth, S.; Bats, J. W.; Trauner, D.; Giester, G.; Mulzer, J. Angew. Chem., Int. Ed. 1999, 38, 2015.
7. "Practical Synthesis of (-)-Morphine." Mulzer, J.; Trauner, D. Chirality 1999, 11, 475.
6. "About the Use of Molecular Workbenches and Platforms in Organic Synthesis." Mulzer, J., Schein, K.; Bohm, I.; Trauner, D. Pure Appl. Chem. 1998, 70, 1487.
5. "Synthesis of Enantiomerically Pure Morphine Alkaloids: The Hydrophenathrene Route." Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908.
4. "New Ventures in the Construction of Complex Heterocycles: Synthesis of Morphine and Hasubanan Alkaloids." Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mulzer, J. Synthesis 1998, 653.
3. "The Phenanthrenone Approach to Opium Alkaloids: Formal Total Synthesis of Morphine by Sigmatropic Rearrangement." Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 5, 441.
2. "Formal Total Synthesis of (-)-Morphine by Cuprate Conjugate Addition." Mulzer, J.; Duerner, G.; Trauner, D. Angew. Chem., Int. Ed. 1997, 35, 2830.
1. "Stereoselective Insertion of Ketenes into O,O-Acetals: Synthesis of β-Alkoxy Esters and 1,4-Dioxepanones." Mulzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. 1996, 35, 1970.
