Department of Chemistry of Nucleic Acid Components

Dr. hab. Michał Sobkowski, prof. IBCH PAS

Head of Department

msob@ibch.poznan.pl
ext. 1182

Research activity

Research area

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

Keywords

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

Research Projects

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

Selected publications

J. Golebiewska, A. Bartoszewicz, M. Kalek, J. Stawinski: „Second generation of nucleotide analogues”, Phosphorus, Sulfur, Silicon Relat. Elem. 197, 511-514, 2022.
https://doi.org/10.1080/10426507.2021.1989689
D. Baranowski, J. Boryski, T. Ostrowski: „7-(β-D-Ribofuranosyl)-3-methylguanine: Synthesis from guanine and comparative multinuclear NMR studies”, J. Mol. Struct. 1250, 131911, 2022.
https://doi.org/10.1016/j.molstruc.2021.131911
M. Rachwalak, J. Golebiewska, T. Jakubowski, J. Stawinski: „Synthesis of Pyridiniumboranephosphonate Diesters and Related Compounds using Trityl Cation as a Borane Hydride Acceptor”, Synthesis 53, 509-517, 2021.
https://doi.org/10.1055/s-0040-1706569
D. Baraniak, J. Boryski: „Triazole-Modified Nucleic Acids for the Application in Bioorganic and Medicinal Chemistry”, Biomedicines 9, 628, 2021. https://doi.org/10.3390/biomedicines9060628
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.
https://doi.org/10.1021/acs.joc.9b03506
D. Wawrzyniak, G. Framski, P. Januszczyk, T. Ostrowski, D. Baraniak, Z. Jahnz-Wechmann, J. Fogt, A. Manikowski, D. Baranowski, K. Rolle, J. Boryski: 7-(β-D-Ribofuranosyl)guanine and its Analogues Modified in the Sugar Portion: Synthesis and Antiglioma Properties, ChemistrySelect 5, 13370-13375, 2020.
https://doi.org/10.1002/slct.202003393
A. Kraszewski, M. Sobkowski, J. Stawinski: H-Phosphonate Chemistry in the Synthesis of Electrically Neutral and Charged Antiviral and Anticancer Pronucleotides, Frontiers in Chemistry 8, 595738, 2020.
https://doi.org/10.3389/fchem.2020.595738
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.
https://doi.org/10.1016/j.ejmech.2018.12.038
D. Baraniak, P. Ruszkowski, D. Baranowski, G. Framski, J. Boryski: Nucleoside dimers analogs containing floxuridine and thymidine with unnatural linker groups: synthesis and cancer line studies. Part III, Nucleosides Nucleotides Nucleic Acids 38, 980-1005, 2019. https://doi.org/10.1080/15257770.2019.1641206
D. Baraniak, D. Baranowski, P. Ruszkowski, J. Boryski: Nucleoside dimers analogues with a 1,2,3-triazole linkage: conjugation of floxuridine and thymidine provides novel tools for cancer treatment. Part II, Nucleosides Nucleotides Nucleic Acids 38, 807-835, 2019. https://doi.org/10.1080/15257770.2019.1610891
L. Michalska, D. Wawrzyniak, A. Szymanska-Michalak, J. Barciszewski, J. Boryski, D. Baraniak: „Synthesis and biological assay of new 2'-deoxyuridine dimers containing a 1,2,3-triazole linker. Part I”, Nucleosides Nucleotides Nucleic Acids 38, 218-235, 2019. https://doi.org/10.1080/15257770.2018.1514122
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. https://doi.org/10.1021/acs.joc.8b00419
A. 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.
https://doi.org/10.1016/j.ejmech.2017.12.070
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.
https://doi.org/10.1039/C5RA27465F
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. https://doi.org/10.1007/128_2014_562
&
https://doi.org/10.1007/128_2014_563

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Department of Chemistry of Nucleic Acid Components

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Department of Chemistry of Nucleic Acid Components

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