Department of Nucleoside and Nucleotide Chemistry

Dr. habil. Michał Sobkowski 

Head of Department
msob@ibch.poznan.pl
ext. 1182

PhD students:

Technical Staff:

Dr. Grzegorz  Framski

starszy specjalista chemik

Dr. Dagmara Baraniak

adiunkt

Dr. habil. Tomasz Ostrowski

profesor instytutu

Dr. Joanna Romanowska

adiunkt

Researchers:

Justyna Gołębiewska MSc

asystent

Prof. Jerzy Boryski

professor

Prof. Adam Kraszewski

professor

Prof. Jacek Stawiński

professor

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

Keywords

Research Projects

Tomasz Modrzyński MSc. BEng.
doktorant 

Media Społecznościowe

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Cooperation

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
e-mail: ibch@ibch.poznan.pl

Sekretariat Dyrektora, tel: 61 852 89 19

Adress