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Group XV

Natural compounds in organicsynthesis [XV]

Head of the group:
Assoc. Professor Dorota Gryko, D.Sc.
e-mail: dorota.gryko@icho.edu.pl
Ph.D., 1997,Institute of OrganicChemistry PAS
Post-doc, 1998-2000,Department of Chemistry, North Carolina StateUniversity, USA
Habilitation, 2008,Institute of OrganicChemistryPAS
Prime Minister Award for PhDthesis, 1998
Post-doc., 2007,Department of Chemistry,University of Texas, Austin, USA
TEAM grant received from the Foundation for Polish Science
WWW: http://ww2.icho.edu.pl/Gryko_group »

Staff:

Post-docs: Dr.Keith ó Proinsias, Dr. Ksenia Maximova

Ph.D. students:

Sabina Pisarek, Dominika Walaszek, Mikołaj Chromiński, Sylwester Kurcoń

Research activities

I. Porphyrinoids as NO-free activators of sGC enzyme

It is the goal of this project to produce new functional mimics for sGC regulation. We believe that chemically modified corrin compounds or other tetrapyrroles may effectively regulate sGC enzyme. To test this hypothesis we will experimentally execute the following aims:

Elaborate new methods for the preparation of vitamin B12 and factor B derivatives as sGC regulators.
Prepare new porphyrin (especially PPIX) derivatives,
Prepare hybrid molecules with dual mode of action e.g. vitamin B12/factor B - porphyrinoid conjugates. The length and nature of spacer will be explored in detail since it was shown that poor in vitro activity of bioconjugates was most likely due to the steric effects associated with the direct conjugation of the peptide to the vitamin.

II. Asymmetric Organocatalysis

Asymmetric synthesis is one of the most important subject in current organic chemistry. In this regard we investigate the development of effective asymmetric reactions using novel organocatalysts. Our research interest involves asymmetric synthesis methodology relying on small organic molecules as catalysts.
We have found that L-prolinethioamides are active catalysts for the direct aldol reaction affording products in good yields and with good enantioselectivity. The addition of an appropriate acid to the reaction effectively enhanced the activity of the catalyst, allowing it to be used in only 2.5 mol %. Furthermore, water is a suitable solvent for the asymmetric aldol reaction. The combination of 1H NMR and ESI MS techniques revealed that the reaction proceeded through an enamine-iminium mechanism.

Selected publications:

1. ó Proinsias, Kurcoń, S.; M.; Gryko, D., Hydrophobic vitamin B12 derivatives: an unprecedented 7-membered lactam formation, Eur. J. Org. Chem. 2011, accepted.

2. ó Proinsias, K., Giedyk, M.; Loska, R.; Chromiński, M.; Gryko, D., Selective modifications of hydrophobic vitamin B12 derivatives at c- and d-positions, J. Org. Chem.2011, 76, 6806-6812.

3. Gryko, D.; Chromiński, M.; Pielacińska, D., Prolinethioamides versus prolinamides in organocatalyzedaldol reaction a comparative study, Symmetry, 2011, 3, 265 – 282.

4. ó Proinsias, K.; Sessler, J.L.; Kurcoń, S.; Gryko, D.,New hydrophobic vitamin B12 derivatives via ring-opening reactions of c-lactone, Org. Lett.2010, 12, 4674-4677.

5. Nowak-Król, A.; Gryko, D.; Gryko, D. T., Meso-Substituted Liquid Porphyrins, Chem. Asian J.2010, 5, 904-909.

6. Gryko, D. T.; Vakuliuk, O.; Gryko, D.; Koszarna, B., Palladium-catalyzed 2-Arylation of Pyrroles, J. Org. Chem.2009, 74, 9517-9520.

7. Gryko, D.; Zimnicka, M.; Lipiński, R. , Brönsted Acids as additives for the Direct Asymmetric Aldol Reaction Catalyzed by L-Prolinethioamides. Direct Evidence for Enamine-Iminium Catalysis, J. Org. Chem.2007, 72, 964-970., J. Org. Chem.2007, 72, 2258-2258.

8. Gryko, D.; Saletra, W. J., Organocatalytic Asymmetric Aldol Reaction in the Presence of Water, Org. Biomol. Chem.2007, 5, 2148-2153.

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