Department of Nucleoside and Nucleotide Chemistry

Dr. habil. Michał Sobkowski 

Head of Department
ext. 1182

PhD students:

Technical Staff:

Dr. Grzegorz  Framski

starszy specjalista chemik

Dr. Dagmara Baraniak


Dr. habil. Tomasz Ostrowski

profesor instytutu

Dr. Joanna Romanowska



Justyna Gołębiewska MSc


Prof. Jerzy Boryski


Prof. Adam Kraszewski


Prof. Jacek Stawiński


Affiliated professors :

  • J. Golebiewska, J. Stawinski: „Reaction of Boranephosphonate Diesters with Pyridines or Tertiary Amines in the Presence of Iodine: Synthetic and Mechanistic Studies”, J. Org. Chem., 85, 4312-4323, 2020. 

  • J. Romanowska, K. Kolodziej, M. Sobkowski, M. Rachwalak, T. Jakubowski, J. Golebiewska, A. Kraszewski, J. Boryski, A. Dabrowska, J. Stawinski: „Aryl H-phosphonates. 19. New anti-HIV pronucleotide phosphoramidate diesters containing amino- and hydroxypyridine auxiliaries”. Eur.J.Med.Chem. 164:47-58, 2019. 

  • J. Golebiewska, M. Rachwalak, T. Jakubowski, J. Romanowska, J. Stawinski: „Reaction of Boranephosphonate Diesters with Amines in the Presence of Iodine: The Case for the Intermediacy of H-Phosphonate Derivatives”, J. Org. Chem., 83, 5496-5505, 2018.

  • Szymanska-Michalak, D. Wawrzyniak, G. Framski, J. Stawinski, J. Barciszewski, A. Kraszewski: „New antiglioma zwitterionic pronucleotides with an FdUMP framework”, Eur. J. Med. Chem., 144, 682-691, 2018.

  • M. Materna, J. Stawinski, A. Kiliszek, W. Rypniewski, M. Sobkowski: „Oxyonium phosphobetaines - unusually stable nucleophilic catalyst-phosphate complexes formed from H-phosphonates and N-oxides”, RSC Adv., 6, 14448-14451, 2016. 

  • Z. Jahnz-Wechmann, G. Framski, P. Januszczyk, J. Boryski: „Bioactive fused heterocycles: Nucleoside analogs with an additional ring”. Eur. J. Med. Chem. 97, 388-396, 2015.

  • M. Sobkowski, A. Kraszewski, J. Stawinski: „Recent Advances in H-Phosphonate Chemistry. Part 1. H-Phosphonate Esters: Synthesis and Basic Reactions”, „Part 2. Synthesis of C-Phosphonate Derivatives”, Topics in Current Chemistry, 137-177 & 179-216, 2015.

  • J. Romanowska, M. Sobkowski, A. Szymanska-Michalak, K. Kolodziej, A. Dabrowska, A. Lipniacki, A. Piasek, Z. M. Pietrusiewicz, M. Figlerowicz, A. Guranowski, J. Boryski, J. Stawinski, A. Kraszewski: „Aryl H-phosphonates 17: (N-Aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity”, J. Med. Chem. 54, 6482-6491, 2011.

  • M. Sobkowski. „Chemistry and stereochemistry of internucleotide bond formation by the H-phosphonate method”, New J. Chem. 34, 854-869, 2010.

  • J. Boryski: „Reactions of Transglycosylation in the Nucleoside Chemistry”, Current Organic Chemistry, 12, 309-325, 2008.

  • G. Framski, Z. Gdaniec, M. Gdaniec, J. Boryski: „A reinvestigated mechanism of ribosylation of adenine under silylating conditions”. Tetrahedron, 62, 10123-10129, 2006.

  • J. Boryski: „Regioselectivity and Mechanism of Transpurination Reactions in the Guanine Nucleosides Series”. J. Chem. Soc., Perkin Trans. 2, 649-652, 1997.

  • J. Jankowska, M. Sobkowski, J. Stawinski, A. Kraszewski: „Studies on aryl H-phosphonates. 1. An efficient method for the preparation of deoxyribo- and ribonucleoside 3'-H-phosphonate monoesters by transesterification of diphenyl H-phosphonate”, Tetrahedron Lett. 35, 3355-3358, 1994. 

  • J. Stawinski, A. Kraszewski: „How to get the most out of two phosphorus chemistries. Studies on H-phosphonates”, Acc.Chem.Res., 35, 952–960, 2002.

  • J. Boryski, B. Golankiewicz, E. De Clercq: „Synthesis and Antiviral Activity of Novel N-Substituted Derivatives of Acyclovir”. J. Med. Chem., 31, 1351-1355, 1988.

  • P.J. Garegg, I. Lindh, T. Regberg, J. Stawinski, R. Stromberg, C. Henrichson: „Nucleoside H-phosphonates. III. Chemical synthesis of oligonucleotides by the hydrogenphosphonate approach”. Tetrahedron Lett. 27, 4051-4054, 1986.

  • R. Crea, A. Kraszewski, T. Hirose, K. Itakura: „Chemical synthesis of genes for human insulin”, Proc. Natl. Acad. Sci. USA, 75, 5765–5769, 1978.

  • K.J. Marians, R. Wu, J. Stawinski, T. Hozumi, S.A. Narang: „Cloned synthetic lac operator DNA is biologically active”, Nature, 263, 744–748, 1976.

Selected publications

  • Chemical architecture of fluorinated nucleoside dimers containing 1,2,3-triazole linker of potential use in molecular biology and medicine. SONATA 15 (2019/35/D/NZ7/03637), PI: Dagmara Baraniak, PhD

  • Exploring second generation of nucleotide analogues containing phosphoranesulfen- or phosphoraneselenamides as new structural motives. PRELUDIUM 16 (2018/31/N/ST5/03589), PI: Justyna Gołębiewska, MSc


Research activity

  • bioorganic chemistry,
  • organophosphorus chemistry,
  • stereochemistry,
  • reaction mechanisms,
  • nucleosides,
  • nucleotides,
  • nucleoside analogues,
  • nucleotide analogues,
  • nucleoside synthesis,
  • pronucleosides,
  • pronucleotides,
  • oligonucleotides,
  • nucleic acids,
  • acyclic nucleosides,
  • 1,2,3-triazole nucleosides,
  • antiviral activity,
  • anticancer activity,
  • enzyme-substrate interactions,
  • transglycosylation,
  • anti-HIV pronucleotides,
  • anti-cancer pronucleotides,
  • H-phosphonates,
  • phosphorus stereochemistry

Chemistry of nucleotides

  • basic research on the methods of synthesis, chemical and physicochemical properties of H-phosphonates with particular emphasis on nucleoside H-phosphonates and their analogues

  • design and synthesis of new nucleotide compounds (e.g., pronucleotides) with potential antiviral (e.g., anti-HIV) or anti-tumor activity

  • studies on metabolic pathways of pronucleotides in various chemical and physiological environments

  • chemistry and stereochemistry of P-chiral nucleotide analogues

  • intramolecular catalysis in the stereospecific synthesis of internucleotide bonds

Chemistry of nucleosides

  • search for new approaches towards synthesis of nucleobases and nucleosides (controlled degradation, rearrangements)

  • synthesis and characterization of nucleoside analogues of potential biological activity, mainly ring analogs of pyrimidine and purine, 7-regioiomers of purine nucleosides, acyclonucleosides, 2’-C-alkylribofuranosides, and analogs od dinucleoside monophosphates, in which internucleotide bond has been replaced with triazole moiety

  • synthesis and biological activity of analogs of dinucleoside monophosphates, in which internucleotide bond has been replaced with 1,2,3-triazole moiety

  • study on the mechanism and applications of transglycosylation reactions

Research area


Research Projects

Tomasz Modrzyński MSc. BEng.

Media Społecznościowe

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Institute of Bioorganic Chemistry,
Polish Academy of Sciences
Z. Noskowskiego 12/14
61-704 Poznań
tel centrala: (+48) 61 852 85 03
fax: (+48) 61 852 05 32

Sekretariat Dyrektora, tel: 61 852 89 19