Medicinal Chemistry

Chemical Biology

Organic Chemistry

Bioorganic Chemistry

Physical-Organic Chemistry

Contact
Telephone: +45 6550 3603
Email: mecinovic@sdu.dk
University of Southern Denmark
Department of Physics, Chemistry and Pharmacy
Campusvej 55
Odense 5230
Denmark



Academic Career
09/2018 – present University of Southern Denmark
Department of Physics, Chemistry and Pharmacy
Associate Professor in Medicinal Chemistry

10/2011 – 08/2018 Radboud University
Institute for Molecules and Materials
Assistant Professor of Chemical Biology



Education
09/2009 – 08/2011 Harvard University
Department of Chemistry and Chemical Biology
Postdoctoral Fellow
Research Advisor: Professor George M. Whitesides

09/2005 - 08/2009 University of Oxford
Chemistry Research Laboratory
PhD in Organic Chemistry
Research Advisor: Professor Christopher J. Schofield, FRS

10/2000 - 06/2005 University of Ljubljana
Faculty of Chemistry and Chemical Technology
BSc in Chemistry (with highest distinction 10.00/10.00)



List of Publications
1. 3-(Dimethylamino)propenoate-Based Regioselective Synthesis of 1,4-Disubstituted 5-
Hydroxy-1H-Pyrazoles; D. Kralj, J. Mecinović, D. Bevk, U. Grošelj, B. Stanovnik, J. Svete; Heterocycles 2006, 68, 897-914.

2. Asparaginyl Hydroxylation of the Notch Ankyrin Repeat Domain by Factor Inhibiting Hypoxia-inducible Factor; M. L. Coleman, M. A. McDonough, K. S. Hewitson, C. Coles, J. Mecinović, M. Edelmann, K. M. Cook, M. E. Cockman, D. E. Lancaster, B. M. Kessler, N. J. Oldham, P. J. Ratcliffe, C. J. Schofield; J. Biol. Chem. 2007, 282, 24027-24038.

3. Kinetic Rationale for Selectivity toward N- and C-terminal Oxygen-dependent Degradation Domain Substrates Mediated by a Loop Region of Hypoxia-Inducible Factor Prolyl Hydroxylases; E. Flashman, E. A. L. Bagg, R. Chowdhury, J. Mecinović, C. Loenarz, M. A. McDonough, K. S. Hewitson, C. J. Schofield; J. Biol. Chem. 2008, 283, 3808-3815.

4. ESI-MS Studies on Prolyl Hydroxylase Domain 2 Reveal a New Metal Binding Site; J. Mecinović, R. Chowdhury, B. M. R. Liénard, E. Flashman, M. R. G. Buck, N. J. Oldham, C. J. Schofield; ChemMedChem 2008, 3, 569-572.

5. Inhibitor Scaffolds for the 2-Oxoglutarate-Dependent Histone Lysine Demethylases; N. R. Rose, S. S. Ng, J. Mecinović, B. M. R. Liénard, S. H. Bello, Z. Sun, M. A. McDonough, U. Oppermann, C. J. Schofield; J. Med. Chem. 2008, 51, 7053-7056.

6. Evidence that Thienamycin Biosynthesis Proceeds via C-5 Epimerization: ThnE Catalyzes the Formation of (2S,5S)-trans-Carboxymethylproline; R. B. Hamed, E. T. Batchelar, J. Mecinović, T. D. W. Claridge, C. J. Schofield; ChemBioChem 2009, 10, 246-250.

7. Triflic Anhydride-Mediated Synthesis of Oxazoles; A. Thalhammer, J. Mecinović, C. J. Schofield; Tetrahedron Lett. 2009, 50, 1045-1047.

8. Evidence for a Stereoelectronic Effect in Human Oxygen Sensing; C. Loenarz, J. Mecinović, R. Chowdhury, L. A. McNeill, E. Flashman, C. J. Schofield; Angew. Chem. Int. Ed. 2009, 48, 1784-1787.

9. Iron-Mediated Cleavage of C-C Bonds in Vicinal Tricarbonyl Compounds in Water; J. Mecinović, R. B. Hamed, C. J. Schofield; Angew. Chem. Int. Ed. 2009, 48, 2796-2800.

10. Application of a Proteolysis/Mass Spectrometry Method For Investigating the Effects of Inhibitors on Hydroxylase Structure; C. J. Stubbs, C. Loenarz, J. Mecinović, K. K. Yeoh, N. Hindley, B. M. Liénard, F. Sobott, C. J. Schofield, E. Flashman; J. Med. Chem. 2009, 52, 2799-2805.

11. Direct Analysis of Enzyme-Catalyzed DNA Demethylation; A. A. Karkhanina, J. Mecinović, M. U. Musheev, S. M. Krylova, A. P. Petrov, K. S. Hewitson, E. Flashman, C. J. Schofield, S. N. Krylov; Anal. Chem. 2009, 81, 5871-5875.

12. Stuctural Basis for Binding of Hypoxia-Inducible Factor by the Oxygen Sensing Prolyl Hydroxylases; R. Chowdhury, M. A. McDonough, J. Mecinović, C. Loenarz, E. Flashman, K. S. Hewitson, C. Domene, C. J. Schofield; Structure 2009, 17, 981-989.

13. Use of Mass Spectrometry to Probe the Nucleophilicity of Cysteinyl-Residues of Prolyl Hydroxylase Domain 2; J. Mecinović, R. Chowdhury, E. Flashman, C. J. Schofield; Anal. Biochem. 2009, 393, 215-221.

14. Epidithiodiketopiperazines Block the Interaction Between Hypoxia Inducible Factor-1α (HIF-1α) and p300 by a Zinc Ejection Mechanism; K. M. Cook, S. T. Hilton, J. Mecinović, W. B. Motherwell, W. D. Figg, C. J. Schofield; J. Biol. Chem. 2009, 284, 26831-26838.

15. A Mouse Model for the Metabolic Effects of the Human Fat Mass and Obesity Associated FTO Gene; C. Church, S. Lee, E. A. L. Bagg, J. S. McTaggart, R. Deacon, T. Gerken, A. Lee, L. Moir, J. Mecinović, M. M. Quwailid, C. J. Schofield, F. M. Ashcroft, R. D. Cox; PLoS Genetics 2009, 5, e1000599.

16. 2-Oxoglutarate Analogue Inhibitors of Prolyl Hydroxylase Domain 2; J. Mecinović, C. Loenarz, R. Chowdhury, C. J. Schofield; Bioorg. Med. Chem. Lett. 2009, 19, 6192-6195.

17. Inhibition of Histone Lysine Demethylase JMJD2A by Ejection of Structural Zn(II); R. Sekirnik, N. R. Rose, A. Thalhammer, P. T. Seden, J. Mecinović, C. J. Schofield; Chem. Commun. 2009, 42, 6376-6378.

18. Therapeutic Manipulation of the HIF Hydroxylases; S. Nagel, N. P. Talbot, J. Mecinović, T. G. Smith, A. M. Buchan, C. J. Schofield; Antiox. Redox Signal. 2010, 12, 481-501.

19. Selective Inhibitors of the JMJD2 Histone Demethylases: Combined Nondenaturing Mass Spectrometric Screening and Crystallographic Approaches; N. R. Rose, E. C. Y. Woon, G. L. Kingham, O. N. F. King, J. Mecinović, I. J. Clifton, S. S. Ng, J. Talib-Hardy, U. Oppermann, M. A. McDonough, C. J. Schofield; J. Med. Chem. 2010, 53, 1810-1818.

20. Carboxymethylproline Synthase Catalysed Syntheses of Functionalised N-Heterocycles; R. B. Hamed, J. Mecinović, C. Ducho, T. D. W. Claridge, C. J. Schofield; Chem. Commun. 2010, 46, 1413-1415.

21. 2-Oxoglutarate Oxygenases Are Inhibited By A Range Of Transition Metals; R. Sekirnik, N. R. Rose, J. Mecinović, C. J. Schofield; Metallomics 2010, 2, 397-399.

22. Selective Inhibition of Histone Demethylase JMJD2E by 3-Substituted Pyridine 2,4-Dicarboxylates; A. Thalhammer, J. Mecinović, C. Loenarz, A. Tumber, N. R. Rose, T. D. Heightman, C. J. Schofield; Org. Biomol. Chem. 2011, 9, 127-135.

23. Studies on the Reaction of Nitric Oxide with the Hypoxia-Inducible Factor Prolyl Hydroxylase Domain 2 (EGLN1); R. Chowdhury, E. Flashman, J. Mecinović, H. B. Kramer, B. M. Kessler, Y. M. Frapart, J. L. Boucher, I. J. Clifton, M. A. McDonough, C. J. Schofield; J. Mol. Biol. 2011, 410, 268-279.

24. Fluoroalkyl and Alkyl Chains Have Similar Hydrophobicities in Binding to the ‘‘Hydrophobic Wall’’ of Carbonic Anhydrase; J. Mecinović, P. W. Snyder, K. A. Mirica, S. Bai, E. T. Mack, R. L. Kwant, D. T. Moustakas, A. Heroux, and G. M. Whitesides; J. Am. Chem. Soc. 2011, 133, 14017-14026.

25. Mechanism of the Hydrophobic Effect in the Biomolecular Recognition of Arylsulfonamides by Carbonic Anhydrase; P. W. Snyder, J. Mecinović, D. T. Moustakas, S. W. Thomas III, M. Harder, E. T. Mack, M. R. Lockett, A. Héroux, W. Sherman, G. M. Whitesides; Proc. Natl. Acad. Sci. USA. 2011, 108, 17889-17894.

26. Activation of Hypoxia-Inducible Factor by Di-Methyl Oxalyl Glycine (DMOG) Increases Neovascularization within Ischaemic Myocardium in a Porcine Coronary Artery Occlusion Model; D. J. S. Kelly, A. C. Morton, N. D. Arnold, J. Mecinović, C. J. Schofield, H. Lupton, K. Al-Lamee, D. C. Crossman, J. Gunn, A. Gershlick; J. Clin. Experiment. Cardiol. 2011, 2, 148.

27. Crotonase Catalysis Enables Flexible Production of Functionalized Prolines and Carbapenams; R. B. Hamed, L. Henry, J. R. Gomez-Castellanos, J. Mecinović, C. Ducho, J. L. Sorensen, T. D. W. Claridge, C. J. Schofield; J. Am. Chem. Soc. 2012, 134, 471-479.

28. Dual-Action Inhibitors of HIF Prolyl Hydroxylases That Induce Binding of a Second Iron Ion; K. K. Yeoh, M. C. Chan, A. Thalhammer, M. Demetriades, R. Chowdhury, Y. M. Tian, I. Stolze, L. A. McNeill, M. K. Lee, E. C. Y. Woon, M. M. Mackeen, A. Kawamura, P. J. Ratcliffe, J. Mecinović, C. J. Schofield; Org. Biomol. Chem. 2013, 11, 732-745.

29. Hydroxylamine as an Oxygen Nucleophile: Substitution of Sulfonamide by Hydroxyl Group in Benzothiazole-2-sulfonamides; J. J. A. G. Kamps, R. Belle, J. Mecinović; Org. Biomol. Chem. 2013, 11, 1103-1108.

30. Evidence That the Catenane Form of CS2 Hydrolase is not an Artefact; M. B. van Eldijk, I. van Leeuwen, V. A. Mikhailov, L. Neijenhuis, H. R. Harhangi, J. C. M. Van Hest, M. S. M. Jetten, H. J. M. Op den Camp, C. V. Robinson, J. Mecinović; Chem. Commun. 2013, 49, 7770-7772.

31. The Effect of the Length of Histone H3K4me3 on the Recognition by Reader Proteins; B. Pieters, R. Belle, J. Mecinović; ChemBioChem 2013, 18, 2408-2412.

32. Thermodynamic Investigation of Z33-Antibody Interaction Leads to Selective Purification of Human Antibodies; M. B. van Eldijk, F. C. M. Smits, J. C. Thies, J. Mecinović, J. C. M. van Hest; J. Biotechnol. 2014, 179, 32-41.

33. Triphenylphosphine-catalysed Amide Bond Formation Between Carboxylic Acids and Amines; D. C. Lenstra, F. P. J. T. Rutjes, J. Mecinović; Chem. Commun. 2014, 50, 5763-5766.

34. Stabilisation of 2,6-Diarylpyridinium Cation by Through-Space Polar-π Interactions; J. Simó Padial, R. de Gelder, C. Fonseca Guerra, F. M. Bickelhaupt, J. Mecinović; Chem. Eur. J. 2014, 20, 6268-6271.

35. Catenane versus Ring: Do both Assemblies of CS2 Hydrolase Exhibit the same Stability and Catalytic Activity?; M. B. van Eldijk, B. J. Pieters, V. A. Mikhailov, C. V. Robinson, J. C. M. van Hest, J. Mecinović; Chem. Sci. 2014, 5, 2879-2884.

36. Transmission Electron Microscopy Enables the Reconstruction of the Catenane and Ring Forms of CS2 Hydrolase; J. C. Wang, A. Zlotnick, J. Mecinović; Chem. Commun. 2014, 50, 10281-10283.

37. Zirconocene Dichloride-Catalysed Amide Bond Formation Between Carboxylic Esters and Amines; D. C. Lenstra, D. T. Nguyen, J. Mecinović; Tetrahedron 2015, 71, 5547-5553.

38. The Role of Electrostatic Interactions in Binding of Histone H3K4me2/3 to the Sgf29 Tandem Tudor Domain; B. J. G. E. Pieters, E. Meulenbroeks, R. Belle, J. Mecinović; PLoS One 2015, 10, e0139205.

39. Chemoselective Calcium-Catalysed Direct Amidation of Carboxylic Esters; D. T. Nguyen, D. C. Lenstra, J. Mecinović; RSC Adv. 2015, 5, 77658-77661.

40. Chemical Basis for the Recognition of Trimethyllysine by Epigenetic Reader Proteins; J. J. A. G. Kamps, J. Huang, J. Poater, C. Xu, B. J. G. E. Pieters, A. Dong, J. Min, W. Sherman, T. Beuming, F. M. Bickelhaupt, H. Li, J. Mecinović; Nat. Commun. 2015, 6, 8911.

41. Natural Supramolecular Protein Assemblies; B. J. G. E. Pieters, M. B. van Eldijk, R. J. M. Nolte, J. Mecinović; Chem. Soc. Rev. 2016, 45, 24-39.

42. Cation-π Interactions Contribute to Substrate Recognition in γ-Butyrobetaine Hydroxylase Catalysis; J. J. A. G. Kamps, A. Khan, H. Choi, R. K. Lesniak, J. Brem, A. M. Rydzik, M. A. McDonough, C. J. Schofield, T. D. W. Claridge, J. Mecinović; Chem. Eur. J. 2016, 22, 1270-1276

43. Multicolor Photoluminescence Including White-Light Emission by a Single Host-Guest Complex; Q.-W. Zhang, D. Li, X. Li, P. B. White, J. Mecinović, X. Ma, H. Ågren, R. J. M. Nolte, H. Tian; J. Am. Chem. Soc. 2016, 138, 13541-13550.

44. Substrate Scope for Trimethyllysine Hydroxylase Catalysis; A. H. K. Al Temimi, B. J. G. E. Pieters, Y. V. Reddy, P. B. White, J. Mecinović; Chem. Commun. 2016, 52, 12849-12852.

45. Evidence That Trimethyllysine Hydroxylase Catalyzes the Formation of (2S,3S)-3-Hydroxy-Nε-trimethyllysine; Y. V. Reddy, A. H. K. Al Temimi, P. B. White, J. Mecinović; Org. Lett. 2017, 19, 400-403.

46. Fluorinated Trimethyllysine as a 19F NMR Probe for Trimethyllysine Hydroxylase Catalysis; Y. V. Reddy, A. H. K. Al Temimi, J. Mecinović; Org. Biomol. Chem. 2017, 15, 1350-1354.

47. Polymethylhydrosiloxane as a Green Reducing Agent in Organophosphorus-Catalysed Amide Bond Formation; D. F. J. Hamstra, D. C. Lenstra, T. Koenders, F. P. J. T. Rutjes, J. Mecinović, Org. Biomol. Chem. 2017, 15, 6426-6432.

48. Stabilization of 2,6-Diarylanilinum Cation by Through-Space Cation–π Interactions; J. Simó Padial, J. Poater, D. T. Nguyen, P. Tinnemans, F. M. Bickelhaupt, J. Mecinović, J. Org. Chem. 2017, 82, 9418-9424.

49. Lysine Possesses the Optimal Chain Length for Histone Lysine Methyltransferase Catalysis; A. H. K. Al Temimi, Y. V. Reddy, P. B. White, H. Guo, P. Qian, J. Mecinović; Sci. Rep. 2017, 7, 16148.

50. Investigating D-Lysine Stereochemistry for Epigenetic Methylation, Demethylation and Recognition; R. Belle, A. H. K. Al Temimi, K. Kumar, B. J. G. E. Pieters, A. Tumber, J. E. Dunford, C. Johansson, U. Oppermann, T. Brown, C. J. Schofield, R. J. Hopkinson, R. S. Paton, A. Kawamura, J. Mecinović; Chem. Commun. 2017, 53, 13264-13267.

51. Recognition of shorter and longer trimethyllysine analogues by epigenetic reader proteins. A. H. K. Al Temimi, R. Belle, K. Kumar, J. Poater, P. Betlem, B. J. G. E. Pieters, R. S. Paton, F. M. Bickelhaupt, J. Mecinović; Chem. Commun. 2018, 54, 2409-2412.

52. Inhibition of histone lysine methyltransferases G9a and GLP by ejection of structural Zn(II). D. C. Lenstra, A. H. K. Al Temimi, J. Mecinović; Bioorg. Med. Chem. Lett. 2018, 28, 1234-1238.

53. 2-Oxoglutarate regulates binding of hydroxylated hypoxia-inducible factor to prolyl hydroxylase domain 2. M. I. Abboud, T. E. McAllister, I. K. H. Leung, R. Chowdhury, C. Jorgensen, C. Domene, J. Mecinović, K. Lippl, R. L. Hancock, R. J. Hopkinson, A. Kawamura, T. D. W. Claridge, C. J. Schofield; Chem. Commun. 2018, 54, 3130-3133.

54. Like Heterochromatin Protein 1 partners with ATRX through unique domains to assist Polycomb Repressive Complex 2 function in plants; H. Wang, D. Jiang, E. Axelsson, S. Montgomery, S. Holec, B. J. G. E. Pieters, A. H. K. Al Temimi, J. Mecinović, F. Berger; Mol. Plant 2018, 11, 1038-1052.

55. Structure-Activity Relationship Studies on (R)-PFI-2 Analogs as Inhibitors of Histone Lysine Methyltransferase SETD7. D. C. Lenstra, E. Damen, R. G. G. Leenders, R. H. Blaauw, F. P. J. T. Rutjes, A. Wegert, J. Mecinović; ChemMedChem 2018, 13, 1405-1413.

56. Sustainable Organophosphorus-Catalysed Staudinger Reduction. D. C. Lenstra, P. E. Lenting, J. Mecinović; Green Chem. 2018, 20, 4418-4422.



Awards, Prizes and Scholarships
Faculty Award, University of Ljubljana, 2002
Distinguished Award, University of Ljubljana, 2005
Prešeren Award for the Outstanding BSc Thesis, University of Ljubljana, 2005
Newton-Abraham Studentship in Chemical Sciences, University of Oxford, 2005-2008
Slovenian Academy of Sciences and Arts Scholarship, 2005-2006
Rotary club Ljubljana Scholarship Award, 2005-2006
Lilly Prize for Excellence in Organic Chemistry, University of Oxford, 2006
Ad Futura Scholarship, 2006-2008
Rotary club Čatež Scholarship Award, 2007-2008
ERC Starting Grant, 2017-2022