List of Publications by PD Dr. Michael Hutter

Printed Papers

  1. F.A. Teßeling, M. Hutter, C. Wiek, J.P. Kowalski, A. Rettie, M. Girhard.
    Novel insights into oxidation of fatty acids and fatty alcohols by cytochrome P450 monooxygenase CYP4B1
    Arch. Biochem. Biophys. 679 (2019) 108216 doi:10.1016/
  2. L. König, S. Brixius-Anderko, M. Milhim, D. Ravouli-Abbas, M. Hutter, F. Hannemann, R. Bernhardt.
    Identification and circumvention of bottlenecks in CYP21A2‐mediated premedrol production using recombinant Escherichia coli
    Biotechnol. Bioeng. (2019) doi:10.1002/bit.27246
  3. T. Fehlmann, M.C. Hutter.
    Conservation and Relevance of Pharmacophore Point Types
    J. Chem. Inf. Model. 59 (2019) 1314-1323 doi:10.1021/acs.jcim.8b00757
  4. T. Sagadin, J. Riehm, N. Putkaradze, M.C. Hutter, R. Bernhardt.
    Novel approach to improve progesterone hydroxylation selectivity by CYP106A2 via rational design of adrenodoxin binding
    FEBS J. 286 (2019) 1240-1249 doi:10.1111/febs.14722
  5. N. Putkaradze, M. Litzenburger, M.C. Hutter, R. Bernhardt.
    CYP109E1 from Bacillus megaterium acts as 24- and 25-hydroxylase for cholesterol
    ChemBioChem 20 (2019) 655-658 doi:10.1002/cbic.201800595
  6. T. Sagadin, J.K. Riehm, M. Milhim, M. Hutter, R. Bernhardt.
    Binding modes of CYP106A2 redox partners determine differences in progesterone hydroxylation priduct patterns
    Communications Biology 1 (2018) 99.
  7. M.C. Hutter.
    The current limits in virtual screening
    Future Med. Chem. 10 (2018) 1623-1635.
  8. Y. Khatri, I.K. Jóźwik, M. Ringle, I.A. Ionescu, M. Litzenburger, M.C. Hutter, A.W.H. Thunnissen, R.Bernhardt.
    Structure-based engineering of steroiogenic CYP260A1 for stereo- and regioselective hydroxylation of progesterone
    ACS Chem. Biol. 13 (2018) 1021-1028.
  9. P.J. Bakkes, J.L. Riehm, T. Sagadin, A. Rühlmann, P. Schubert, S. Biemann, M. Girhard, M.C. Hutter, R. Bernhardt, V.B. Urlacher.
    Engineering of versatile redox partner fusions that support monooxygenase activity of functionally diverse cytochrome P450s

    Sci. Rep. 7 (2017) 9570.
  10. J. Nikolaus, K.T. Nguyen, C. Virus, J.L. Riehm, M.C. Hutter, R. Bernhardt.
    Engineeing of CYP106A2 for Steroid 9α- and 6β-hydroxylation

    Steroids 120 (2017) 41-48.
  11. N. Putkaradze, F.M. Kiss, D. Schmitz, J. Zapp, M.C. Hutter, R. Bernhardt.
    Biotransformation of prednisone and dexamethasone by cytochrome P450 based systems – identification of new potential drug candidates
    J. Biotechnol. 242 (2017) 101-110.
  12. X. Yang, M. Hutter, W.W.B. Goh, M. Bureik.
    CYP4Z1 – A human cytochrome P450 enzyme that might provide the key to treat breast cancer
    Cur. Pharm. Design 23 (2017) 2060-2064.
  13. T. Sagadin, J. Riehm, M. Hutter, R. Bernhardt.
    Optimization of redox partner interactions with cytochromes P450 (CYP)
    J. New Biotechnol. 33 (2016) S102.
  14. S. Janoscha, Y. Carius, M. Hutter, C.R.D. Lancaster, R. Bernhardt.
    Crystal Structure of CYP106A2 in Substrate-Free and Substrate-Bound Form

    ChemBioChem 17 (2016) 852-860.
  15. A. Thoman, J. Zapp, M. Hutter, M. Empting and R. W. Hartmann.
    Steering the azido-tetrazole equilibrium of 4-azidopyrimidines via substituent variation – implications for drug design and azide-alkyne cycloadditions
    Org. Biomol. Chem 13 (2015) 10620-10630. DOI: 10.1039/C5OB01006C
  16. A. Mosa, M.C. Hutter, J. Zapp, R. Bernhardt, F. Hannemann.
    Regioselective Acetylation of C21 Hydroxysteroids by the bacterial Chloramphenicol Acetyltransferase I
    ChemBioChem 16 (2015) 1670-1679. DOI: 10.1002/cbic.201500125
  17. Y. Khatri, F. Hannemann, M. Girhard, R. Kappl, M. Hutter , V.B. Urlacher, R. Bernhardt.
    A natural heme-signature variant of CYP267A1 from Sorangium cellulosum So ce56 executes diverse ω-hydroxylation
    FEBS J. 282 (2015) 74-88.
  18. M.C. Hutter, C. Brengel, M. Negri, C. Henn, C. Zimmer, R.W. Hartmann, M. Empting, A. Steinbach
    Mechanistic details for anthraniloyl transfer in PqsD: the initial step in HHQ biosynthesis
    J. Mol. Model. 20 (2014) 2255-2264.
  19. T. Will, M.C. Hutter, J. Jauch, V. Helms
    Batch tautomer generation with MolTPC
    J. Comput. Chem. 34 (2013) 2485-2492.
  20. S. Janocha, J. Zapp, M. Hutter, M. Kleser, R. Bernhardt
    Resin acid conversion with CYP105A1: An enzyme with potential for the production of pharmaceutically relevant diterpenoids
    ChemBioChem 14 (2013) 467-473.
  21. A. Hobler, N. Kagawa, M.C. Hutter, S.A. Wudy, F. Hannemann, R. Bernhardt
    Human aldosterone synthase: Recombinant expression in E. Coli and purification enables a detailed biochemical analysis of the protein on the molecular level
    J. Steroid Biochem. Mol. Biol. 132 (2012) 57-65.
  22. M. Kleser, F. Hannemann, M. Hutter, J. Zapp, R. Bernhardt
    CYP105A1 mediated 3-hydroxylation of glimepiride and glibenclamide using a recombinant Bacillus megaterium whole-cell catalyst
    J. Biotechnol. 157 (2012) 405-412.
  23. T.T. Ly, Y. Khatri, J. Zapp, M.C. Hutter, R. Bernhardt
    CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase
    Appl. Microbiol. Biotechnol. 95 (2012) 123-133.
  24. M.C. Hutter
    Determining the Randomness of Descriptors in Linear Regression Equations with Respect to the Data Size
    J. Chem. Inf. Model. 51 (2011) 3099-3104.
  25. M. Carbon-Mangels, M.C. Hutter
    Selecting Relevant Descriptors for Classification by Bayesian Estimates: A Comparison with Decision Trees and Support Vector Machines Approaches for Disparate Data Sets
    Mol. Inf. 30 (2011) 885-895.
  26. M.C. Hutter
    Graph-Based Similarity Concepts in Virtual Screening
    Future Med. Chem. 3 (2011) 485-501.
  27. W. Gu, B. Zhou, T. Geyer, M. Hutter, H. Fang, V. Helms
    Design of a Gated Molecular Proton Channel
    Angewandte Chemie Int. Ed. 50 (2011) 768-771.
    Angewandte Chemie 123 (2011) 794-797.
  28. Y. Khatri, M. Girhard, A. Romankiewicz, M. Ringle, F. Hannemann, V.B. Urlacher, M.C. Hutter, R. Bernhardt
    Regioselective Hydroxylation of Norisoprenoids by CYP109D1 from Sorangium cellulosum So ce56
    Appl. Microbiol. Biotechnol. 88 (2010) 485-495.
  29. M.C. Hutter
    ChemMedChem 5 (2010) 306-307.
    Book Review: Molecular Descriptors for Chemoinformatics (2nd. ed.)
    by Roberto Todeschini and Viviana Consonni
    Wiley-VCH, Weinheim Germany, 2009.
  30. M.C. Hutter
    QSAR – Old And New Directions in
    Chemical Modelling: Applications and Theory Vol. 6 pp. 112-130.
    Ed. M.Springborg, RSC Publishing, Cambridge UK, 2009.
  31. M. Krier, M.C. Hutter
    Bioisosteric Similarity of Molecules Based on Structural Alignment and Observed Chemical Replacements in Drugs
    J. Chem. Inf. Model. 49 (2009) 1280-1297.
  32. M.C. Hutter
    In Silico Prediction of Drug Properties
    Curr. Med. Chem. 16 (2009) 189-202.
  33. N. Schneider, C. Jäckels, C. Andres, M.C. Hutter
    Gradual in Silico Filtering for Druglike Substances
    J. Chem. Inf. Model. 48 (2008) 613-628.
  34. M.C. Hutter
    Separating Drugs from Nondrugs: A Statistical Approach Using Atom Pair Distributions
    J. Chem. Inf. Model. 47 (2007) 186-194.
  35. M. Gepp, M.C. Hutter
    Determination of hERG Channel Blockers Using a Decision Tree
    Bioorg. Med. Chem. 14 (2006) 5325-5332.
  36. C. Andres, M.C. Hutter
    CNS Permeability of Drugs Predicted by a Decision Tree
    QSAR Comb. Sci. 25 (2006) 305-309.
  37. M.C. Hutter
    Stability of the Guanine-Cytosine Radical Cation in DNA Base Pair Triplets
    Chem. Phys. 326 (2006) 240-245.
  38. V. Helms, M. Hutter, W. Gu
    Was hat das Eiweiß in einem Computer zu suchen?
    Magazin Forschung (2005) 28-32.
    pdf version
  39. M. C. Hutter, R. W. Hartmann
    QSAR of Human Steroid 5α-Reductase Inhibitors: Where are the differences between isoenzyme type 1 and 2?
    QSAR Comb. Sci. 23 (2004) 406-415.
  40. E. Olkhova, M. C. Hutter, M. A. Lill, V. Helms, H. Michel
    Dynamic Water Networks in Cytochrome c Oxidase from Paracoccus denitrificans Investigated by Molecular Dynamics Simulations
    Biophys. J. 86 (2004) 1873-1889.
  41. M. C. Hutter
    Prediction of Blood-Brain Barrier Permeation Using Quantum Chemically Derived Information
    J. Comput.-Aided Mol. Des. 17 (2003) 415-433.
  42. M. C. Hutter, V. Helms
    Mechanism of Phosphoryl Transfer in Kinases Investigated by Semiempirical Calulations
    Int. J. Quant. Chem. 95 (2003) 479-486.
  43. J. E. T. Corrie, A. Barth, V. R. N. Munasinghe, D. R. Trentham, M. C. Hutter
    Photolytic Cleavage of 1-(2-Nitrophenyl)ethyl Ethers Involves Two Parallel Pathways and Product Release Is Rate-Limited by Decomposition of a Common Hemiacetal Intermediate
    J. Am. Chem. Soc. 125 (2003) 8546-8554.
  44. M. C. Hutter, J. Krebs, J. Meiler, C. Griesinger, E. Carafoli, V. Helms
    A Structural Model of the Complex between Phospholamban and the Calcium Pump of Sarcoplasmic Reticulum obtained by Molecular Mechanics
    Chem. Bio. Chem. 3 (2002) 1200-1208.
  45. M. C. Hutter, V. Helms
    Mechanism of Phosphorylation of Natural Nucleosides and Anti-HIV Analogs by Nucleoside Diphosphate Kinase is Independent of their Sugar Substituents
    Chem. Bio. Chem. 3 (2002) 643-651.
  46. J. M. Hughes, M. C. Hutter, J. R. Reiners, N. S. Hush
    Modeling the Bacterial Photosynthetic Reaction Centre.
    4. The Structural, Electrochemical, and Hydrogen-Bonding Properties of 23 Mutants of Rhodobacter sphaeroides

    J. Am. Chem. Soc. 123 (2001) 8550-8563.
  47. S. Bartoscheck, G. Buurman, R. K. Thauer, B. H. Geierstanger, J. P. Weyrauch, C. Griesinger, M. Nilges, M. C. Hutter, V. Helms
    Re-face Stereospecificity of Methylenetetrahydromethanopterin Dehydrogenases and Methylenetetrahydrofolate Dehydrogenases Predetermined by Intrinsic Properties of the Substrate
    Chem. Bio. Chem. 2 (2001) 530-541.
  48. M. C. Hutter, V. Helms
    Phosphoryl transfer by a concerted reaction mechanism in UMP/CMP-kinase
    Protein Sci. 9 (2000) 2225-2231.
  49. J. R. Reimers, M.C. Hutter, J. M. Hughes, N. S. Hush
    Nature of the Special-Pair Radical Cation in Bacterial Photosynthesis
    Int. J. Quant. Chem. 80 (2000) 1224-1243.
  50. M. A. Lill, M. C. Hutter, V. Helms
    Accounting for Environmental Effects in ab initio Calculations of Proton Transfer Barriers
    J. Phys. Chem. A 104 (2000) 8283-8289.
  51. M. C. Hutter, V. Helms
    Influence of key residues on the reaction mechanism of the cAMP-dependent protein kinase
    Protein Sci. 8 (1999) 2728-2733.
  52. M. C. Hutter, J. M. Hughes, J. R. Reimers, N. S. Hush
    Modeling the bacterial photosynthetic reaction centre:
    2. A combined quantum mechanical/molecular mechanical study on the structure of the cofactors in the reaction centres of purple bacteria

    J. Phys. Chem. B 103 (1999) 4906-4915.
  53. M. C. Hutter, J. R. Reimers, N. S. Hush
    Modeling the bacterial photosynthetic reaction centre:
    1. Magnesium parameters for the semiempirical AM1 method developed using a genetic algorithm

    J. Phys. Chem. B 102 (1998) 8080-8090.
  54. J. R. Reimers, M. Hutter, N. S. Hush
    The Spectroscopy of the Low-Lying Bands in the Special-Pair Radical-Cations of Photosynthetic Reaction Centers
    Photosynth. Res. 55 (1998) 163-171.
  55. M. C. Hutter, J. R. Reimers, N. S. Hush
    Magnesium parameters for the semiempirical AM1 method:
    Development and applications to bacteriochlorophylls

    Proceedings of the 4th Australian Molecular Modelling Conference and Workshop, Macquarie University Press, Sydney, 1998, p.16.
  56. M. Hutter
    Semiempirische MO-Methoden und Anwendungen für Umgebungseffekte
    Doktorarbeit (PhD thesis), Universität Erlangen (Germany), 1997.
  57. M. Hutter, T. Clark
    Stabilities and hydrogen shifts in oxidized DNA base-pairs: ab initio and DFT calculations
    J. Mol. Model. 2 (1996) 261.
  58. M. Hutter, T. Clark
    On the enhanced stability of the guanine-cytosine base-pair radical cation
    J. Am. Chem. Soc. 118 (1996) 7574-7577.


  • M. Hutter
    Similarität von Molekülen auf der Basis von Punktladungen: Optimierung und Anwendung
    at the 8th Molecular-Modelling-Workshop in Darmstadt 1994 (D)
  • M. Hutter
    New Developments of the Numerical SCRF Method for semiempirical methods
    at the Conference on Computational Chemistry in Mariapfarr (Austria) 1995
  • M. Hutter
    Ionized DNA-base-pairs: ab initio calculations
    at the 9th Molecular-Modelling-Workshop Darmstadt
  • M. Hutter
    Magnesium parameters for the semiempirical AM1 method:
    Development and applications to bacteriochlorophylls

    at the 4th Australian Molecular Modelling Workshop in Sydney (AUS) 1998
  • M. Hutter
    The mechanism of phosphoryl transfer in kinases
    at the 36th Symposium for Theoretical Chemistry, Litschau (A) 2000


  • M. Hutter
    Intercalations of mutagenic compounds in DNA – A classical/quantum mechanical method
    at the Fourth Oxford Meeting on Molecular Orbital Methods to Biological and Chemical Problems in Oxford (UK) 1993
  • M. Hutter, T. Clark
    Stabilities and hydrogen shifts in oxidized DNA base-pairs: ab initio and DFT calculations
    at the 10th Molecular-Modelling-Workshop 1996 in Darmstadt (D)
    J. Mol. Model. 2 (1996) 261
  • P. Gedeck, M. Hutter, T. Clark
    Towards an accurate SCRF Solvation model for semiempirical MO methods
    at the International MGMS Meeting on Molecular Interactions in York (UK) 1996
  • M. Hutter
    Modelling of the binding position of dihydrofolate reductase ligands using a combined QM/MM-method
    at the 3rd Australian Molecular Modelling Workshop in Melbourne (AUS) 1997
  • M. C. Hutter, V. Helms
    Mechanism of Phosphoryltransfer of cAMP-Dependent Protein Kinase Studied by Quantum-Chemical Calculations
    at the QBIC’99 Symposium, Warwick (UK) 1999
  • J. M. Hughes, J. R. Reimers, M. C. Hutter and N. S. Hush.
    Modelling the Structural and Vibrational Properties of the Bacterial Photosynthetic Reaction Centres of Rhodobacter Sphaeroides, its Mutants and Rhodospeudomonas Viridis
    at the WATOC Conference, London (UK) 1999
  • M. C. Hutter, V. Helms
    Mechanism of Phosphoryltransfer of cAMP-Dependent Protein Kinase Studied by Quantum-Chemical Calculations
    at the Third European Symposium of the Protein Society, Garmisch-Partenkirchen (D) 1999
  • S. Bartoscheck, G. Buurman, R. K. Thauer, B. H. Geierstanger, J. P. Weyrauch, C. Griesinger, M. Nilges, M. C. Hutter, V. Helms
    Metal-free hydrogenase from methanogenic archaea: Mechanism of substrate activation
    at the Workshop “Computer Simulations and Theory of Biomolecules”, Hünfeld (D) 2001
  • M. C. Hutter, V. Helms
    Evidence for a common mechanism of phosphoryl transfer in all kinases
    at the “Jahrestagung der Deutschen Gesellschaft für Biophysik”, Dresden (D) 2002