CURRICULUM VITAE

Dr. chem. Māris TURKS

Date of birth: March 11, 1976 Place of birth: Jelgava, E-mail: [email protected] Professional Address: Faculty of Materials Science and Applied Chemistry Technical University P. Valdena Str. 3 Riga, LV-1048, Latvia Phone: 371 67089251

Professional experience:

05.2012- Full professor, Riga Technical University, Riga, Latvia 06.2010- Director of the Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Riga, Latvia 06.2007-05.2012 Associate professor, Riga Technical University, Riga, Latvia 12.2006-06.2007 Docent, Riga Technical University, Riga, Latvia 12.2005-12.2006 SNSF Postdoctoral fellow, Stanford University, California, USA, with Prof. Barry M. Trost 02.2005-11.2005 Postdoctoral assistant, Swiss Federal Institute of Technology, Lausanne (EPFL), Switzerland, with Prof. Pierre Vogel 2001-2004 Teaching assistant, organic chemistry, EPFL, Switzerland 1995-2000 Assistant, Faculty of Chemistry, Riga Technical University, Riga, Latvia

Education:

12.2000-01.2005 PhD studies, UNIL/EPFL, Switzerland, with Prof. Pierre Vogel 2001 DEA multinational de Chimie Moléculaire, Ecole Polytechnique, Palaiseau, France (European Master of Molecular Chemistry) 1998-2000 Master of Engineering Sciences in Chemistry (with distinction), Riga Technical University, Latvia 1998-1999 Qualification as high school chemistry teacher, , Latvia 1994-1998 Bachelor of Chemistry (with distinction), University of Latvia, Latvia

Other activities:

06.2015- Deputy Editor of Chemistry of Heterocyclic Compounds 01.2015- Member of the Scientific Council at Riga Technical University (RTU) 04.2014- Member of the Professor Council for Chemistry and Chemical Engineering at RTU 06.2013- Member of the Natural Sciences and Mathematics expert panel at the Latvian Council of Science 2012-2014 Member of RTU Senate, Chair of the Science Commission of RTU Senate 10.2012- Latvian representative at the Division of Organic Chemistry, European Association for Chemical and Molecular sciences 02.2010- Member of the Promotion Council P-01 at RTU 10.2011- Member of the Editorial Board of Scientific Journal of RTU: Materials Sciences and Applied Chemistry

Dr. chem. Māris Turks. Curriculum Vitae

Awards and scholarships: The Latvian Academy of Sciences Gustavs Vanags Prize (in Chemistry), 2016 Full Member of the Latvian Academy of Sciences, 2014 Corresponding Member of the Latvian Academy of Sciences, 2011 Riga Technical University Young Scientist of the Year 2010 Swiss NSF Fellowship for prospective researchers 12.2005-12.2006 for postdoctoral studies at Stanford University Invitation to “Roche Symposium for leading chemists of the next decade”, Basel, Switzerland, October 20-22, 2004. Thieme Poster Prize at International Conference on Organic Synthesis BOS2004 [Balticum Organicum Syntheticum], Riga, Latvia, June 27 - July 1, 2004. Scholarship from The Danish Rectors’ Conference for project in organic chemistry at University of Aarhus, Denmark, 2000. Prize for young scientists from Latvian Academy of Sciences, 1999 and 2001.

Selected research projects (2010 - ): 1) M. Turks (Head of Project). “Organic reactions in and with liquid sulfur dioxide” Latvian Council of Science Grant #12.0291 (2013-2016). 2) M. Turks (Head of Subproject). “Development of Novel Agents for Antitumor and Antimicrobial Therapy” Latvian Council of Science Cooperation Project #14.0593 (2014- 2017). 3) “Synthesis of novel (deaza)purine-triazole conjugates and applications of their fluorescent properties” Latvian-Lithuanian-Taiwanese joint grant # LV-LT-TW/2015/2 // W1935. M. Turks: Head of the Latvian part of the project (2015-2017). 4) “Design and synthesis of triterpenoids modified with cyclic triacylmethanes and heterocycles as additional pharmacophores”. Latvian-Belarus joint project # W1935. M. Turks: Head of the Latvian part of the project (2014-2015). 5) M. Turks (Head of Project). “Synthesis and secondary structure elucidation of novel carbopeptoids and triazole analogs thereof” Latvian Council of Science Grant #09.1557 (2009-2012). 6) M. Turks (Head of Subproject) “Development of multiheterocyclic chemistry for the preparation of new biologically active compounds” Latvian Council of Science Cooperation Project #10.0030 (2010-2013) 7) “Tetrahydroindazoles: synthesis, chemical transformations and biological activity”. Latvian-Belarus joint project. M. Turks: Head of the Latvian part of the project #L7630 (2010-2011) 8) M Turks (Head of Project). Biosynthesis and isolation of macrolide type of antibiotics and antiparasitic agents and production of synthetic derivatives thereof. ERAF 2.1.1.1. project #2010/0278/2DP/2.1.1.1.0/10/APIA/VIAA/045 (2010-2013)

Teaching and research supervision: Supervisor for 2 finalized PhD thesis and 1 active PhD thesis Supervisor for 13 Master’s thesis Supervisor for 28 Bachelor’s thesis

Courses: Modern organic chemistry (PhD students) Selected chapters on heterocyclic chemistry (PhD students) Selected chapters on organic synthesis (Master students) Chemistry and technology of pharmaceutical drugs (Master students) Purification and analysis of organic compounds (Master students) Chemistry experiments and demonstrations (Bachelor students) Technologies for obtaining biologically active substances (Bachelor students)

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Dr. chem. Māris Turks. Curriculum Vitae

Selected publications:

1) Rjabovs, V.; Ostrovskis, P.; Posevins, D.; Kiseļovs, G.; Kumpiņš, V.; Mishnev, A.; Turks, M.* Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly. Eur. J. Org. Chem. 2015, 5572-5584. 2) Turks, M.*; Rolava, E.; Stepanovs, D.; Mishnev, A.; Marković, D. Novel 3-C- aminomethyl-hexofuranose-derived thioureas and their testing in asymmetric catalysis. Tetrahedron: Asymmetry 2015, 26, 952-960. 3) Uzuleņa, J.; Rjabovs, V.; Moreno-Vargas, A. J.; Turks, M.* Synthesis of 1,2,3-triazole- linked glycohybrids in the gluco-, gulo-, and allopyranose series. Chem. Heterocycl. Comp. 2015, 51, 664–671. 4) Stikute, A.; Peipiņš, V.; Turks, M.* Synthesis of allyl sulfoxides from allylsilanes via silyl sulfinates. Tetrahedron Lett. 2015, 56, 4578-4581. 5) Novosjolova, I.; Turks, M.* User friendly synthesis of Vogel’s silyl sulfinate and its application in quantitative GC-MS analysis. Phosphorus, Sulfur Silicon Rel. Elem. 2015, 190, 1251-1256. 6) Lugiņina, J.; Bizdēna, Ē.; Leonciks, A.; Kumpiņš, V.; Grīnšteine, I.; Turks, M.* Synthesis and antibacterial activities of milbemycin A3/A4 5-phthalate and 5-glutarate derivatives. Chem. Heterocycl. Comp., 2015, 50, 1404-1412. 7) Turks, M.*; Vēze, K.; Kiselovs, G.; Mackeviča, J.; Lugiņina, J.; Mishnev, A.; Markovic, D. Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses. Carbohydr. Res. 2014, 391, 82-88. 8) Romanchikova, N.*; Trapencieris, P.; Zemītis, J.; Turks, M.* A novel matrix metalloproteinase-2 inhibitor triazolylmethyl aziridine reduces melanoma cell invasion, angiogenesis and targets ERK1/2 phosphorylation. J. Enzyme Inhib. Med. Chem. 2014, 29, 765-772. 9) Mackeviča, J.; Ostrovskis, P.; Leffler, H.; Nilsson, U. J.; Rudovica, V.; Viksna, A.; Belyakov, S.; Turks, M.* Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins. ARKIVOC 2014, iii, 90-112. 13) Novosjolova, I.; Bizdēna, Ē.; Turks, M.* Application of 2,6-diazidopurine derivatives in the synthesis of thiopurine nucleosides. Tetrahedron Lett. 2013, 54, 6557-6561. 14) Lugiņina, J.; Rjabovs, V.; Belyakov, S.; Turks, M.* A concise synthesis of sugar isoxazole conjugates. Tetrahedron Lett. 2013, 54, 5328-5331. 15) Kovaļovs, A.; Novosjolova, I.; Bizdēna, Ē.; Bižāne, I.; Skardziute, L.; Kazlauskas, K.; Jursenas, S.; Turks, M.* 1,2,3-Triazoles as leaving groups in purine chemistry: a three- step synthesis of N6-substituted-2-triazolyl-adenine nucleosides and photophysical properties thereof. Tetrahedron Lett. 2013, 54, 850-853. 16) Bizdena, E., Belyakov, S., Jure, M., Grinsteine, I., Kumpins, V., Turks, M.* X-Ray structure analysis of a solid solution of milbemycins A3 and A4. Nat. Prod. Res. 2013, 27, 1936-1939. 17) Turks, M.*; Rodins, V.; Rolava, E.; Ostrovskis, P. Belyakov, S. A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate. Carbohydr. Res. 2013, 375, 5-15. 18) Kreituss, I.; Rozenberga, E.; Zemītis, J.; Trapencieris, P.; Romanchikova, N.; Turks, M.* Discovery of aziridine–triazole conjugates as selective MMP-2 inhibitors. Chem. Heterocycl. Comp. 2013, 49, 1108-1117. 19) Turks, M.*; Strakova, I.; Gorovojs, K.; Belyakov, S.; Piven, Y.; Khlebnikava, T.; Lakhvich, F. A facile synthesis of 4-acylamino tetrahydroindazoles via the Ritter reaction. Tetrahedron 2012, 68, 6131-6140. 20) Turks, M.*; Rijkure. I.; Belyakov, S.; Zicāne, D.; Kumpiņš, V.; Bizdēna, Ē.; Meikas, A.; Valkna, A. On differences between racemic and enantiomerically pure forms of aziridine- 2-carboxamide. Chem. Heterocycl. Comp. 2012, 48, 861-868. 21) Lugiņina, J.; Rjabovs, V.; Belyakov, S.; Turks, M.* On Moffatt dehydration of glucose- derived nitro alcohols. Carbohydr. Res. 2012, 350, 86.

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Dr. chem. Māris Turks. Curriculum Vitae

22) Rjabova, J.; Rjabovs, V.; Moreno Vargas, A. J.; Moreno Clavijo, E.; Turks, M.* Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity. Centr. Eur. J. Chem. 2012, 10, 386. 23) Exner, J. C.; Turks, M.; Fonquerne, F.; Vogel, P. Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation. Chem. Eur. J. 2011, 17, 4246. 24) Turks, M.; Fairweather, K. A.; Scopelliti, R.; Vogel, P. Efficient Asymmetric Synthesis of Long-Chain Polyketides Containing up to Ten Contiguous Stereogenic Centres by Double Chain Elongation. Eur. J. Org. Chem. 2011, 3317. 25) Strakova, I.; Kumpiņa, I., Rjabovs, V.; Lugiņina, J, Belyakov, S.; Turks, M.* Resolution, absolute configuration and synthetic transformations of 7-amino-tetrahydroindazolones. Tetrahedron: Asymmetry, 2011, 22, 728. 26) Laclef S., Turks M., Vogel P. Total Synthesis and Determination of the Absolute Configuration of (−)-Dolabriferol. Angew. Chem. Int. Ed. 2010, 49. 8525. 27) Strakova, I.; Turks, M.*; Strakovs, A. Synthesis of triazole-functionalized tetrahydroindazolones by 1,3-dipolar cycloadditions between azides and alkynes. Tetrahedron Lett. 2009, 50, 3046. 28) Turks, M.; Exner, C.; Craita, C.; Vogel. P. Umpolung with Sulfur Dioxide. The Carbon- Carbon Cross-coupling of Electron-rich 1,3-Dienes and Alkenes; Application to the Enantioselective Synthesis of Long-Chain Polyketide Fragments. Synthesis 2009, 1065- 1074. 29) Bouchez, L. C.; Turks, M.; Dubbaka, S. R.; Fonquerne, F.; Craita, C.; Laclef, S.; Vogel, P. Sulfur Dioxide Mediated One-Pot, Four-Component Synthesis of Polyfunctional Sulfones and Sulfonamides, Including Medium-Ring Cyclic Derivatives. Tetrahedron 2005, 61, 11473. 30) Turks, M.; Huang, X.; Vogel, P. Expeditious Asymmetric Synthesis of a Stereoheptad Corresponding to the C(19)-C(27)-Ansa Chain of Ryfamicins; Formal Total Synthesis of Rifamicin S. Chem. Eur. J. 2005, 11, 465. 31) Turks, M.; Murcia, M. C.; Vogel, P. First Asymmetric Synthesis of the Cyclohexanone Subunit of Baconipyrones A and B. Revision of the Published Stucture. Org. Lett. 2004, 6, 3031. 32) Turks, M.; Fonquerne, F.; Vogel, P. Synthesis of Long-Chain Polyketide Fragments by Reaction of 1,3-Dioxy-1,3-Dienes with Allylsilanes: Umpolung with Sulfur Dioxide. Org. Lett. 2004, 6, 1053.

Selected reviews and book chapters:

1) Novosjolova, I.; Bizdena, E.; Turks, M.* Synthesis and applications of azolylpurine and azolylpurine nucleoside derivatives. Eur. J. Org. Chem. 2015, 3629-3649. 2) Marković, D.; Kolympadi, M.; Deguin, B.; Porée, F.-H.; Turks, M. The Isolation and Synthesis of Neodolastane Diterpenoids. Nat. Prod. Rep. 2015, 32, 230-255. 3) Ostrovskis, P.; Mackeviča, J.; Kumpiņš, V.; López, Ó.; Turks, M.* An Alternative, Large Scale Synthesis of 1,2:5,6-Di-O-isopropylidene-α-D-ribo-hex-3-ulofuranose. In Carbohydrate Chemistry: Proven Synthetic Methods; van der Marel, G., Codee, J., Eds.; CRC Press: Boca Raton, London, New York, 2014; Vol. 2, pp 275-281. 4) Rjabovs, V.; Turks, M.* Tetrahydrofuran amino acids of the past decade. Tetrahedron 2013, 69, 10693-10710. 5) Ostrovskis, P.; Volla, C. M. R.; Turks, M.; Markovic, D. Application of Metal Free Click Chemistry in Biological Studies. Curr. Org. Chem. 2013, 17, 610-640. 6) Turks, M.*; Laclef, S.; Vogel, P. Construction of polypropionate fragments in natural product synthesis. In Stereoselective synthesis of drugs and natural products. Andrushko, V.; Andrushko, N., Eds. Wiley-Blackwell, 2013, pp. 271-318. 7) Vogel, P.; Markovic, D.; Turks, M.* Sulfur dioxide: a powerful tool for the stereoselective construction of C-C bonds. In Stereoselective synthesis of drugs and

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natural products. Andrushko, V.; Andrushko, N., Eds. Wiley-Blackwell, 2013, pp.623- 666. 8) Vogel, P.; Turks, M.; Bouchez, L.; Markovic, D.; Varela-Alvarez, A.; Sordo, J. A. New Organic Chemistry of Sulfur Dioxide. Acc. Chem. Res. 2007, 40, 931.

Selected patents and patent applications:

1) Bizdēna, E.; Kumpiņš, V.; Turks, M. Process for isolation of milbemycins A3 and A4. Eur. Pat. Appl. EP2886640 (A1), 2015-06-24. 2) Zhulenkovs, D.; Rudevica, Z.; Leonciks, A.; Jaudzems, K.; Zicāne, D.; Turks, M. N-(3- hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide as a novel inhibitor for Staphylococcus aureus sortase A. Eur. Pat. Appl. EP2875816 (A1), 2015-05-27. 3) Zhulenkovs, D.; Rudevica, Z.; Leonciks, A.; Jaudzems, K.; Zicāne, D.; Turks, M. N'-(2- (3-oxobenzo[d]isothiazol-2(3H)-yl)acetyl)adamantane-1-carbohydrazide as a novel inhibitor for Staphylococcus aureus sortase A. Eur. Pat. Appl. EP2875815 (A1), 2015-05- 27. 4) Zicāne, D.; Turks, M. New process for the preparation of 3-(2,2,2- trimethylhydrazinium) propionate dihydrate. Eur. Pat. EP2282990 (B1), 2011-04-27. See also: (2011-10-12); AT528282 (T) (2011-10-15); EA201001701 (A1) (2011-06-30); CN102036950 (A). 5) Zicāne, D.; Turks, M. Process for preparing 3-(2,2- dimethylhydrazino) methylpropionate. Eur. Pat. EP2282989 (B1), 2011-04-27. See also: (2011-10-12); AT528281 (T) (2011-10-15); EA201001700 (A1) (2011-06-30); CN102036949 (A). 6) Vogel, P.; Bouchez, L.; Dubbaka, S.; Turks, M. Polyfunctional sulfonamides and sulfonates and process for preparing them. Eur. Pat. Appl. EP1447397 A1, 2004-08-18.

Māris Turks November 8, 2015

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