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Group IV

Chemistry of sucrose. Application of simple carbohydrates as chiral building blocks [IV]

Head of the group:
Professor Sławomir Jarosz
e-mail: slawomir.jarosz@icho.edu.pl
Ph.D. in 1979 at the Institute of Organic Chemistry of the Polish Academy of Sciences under Professor Aleksander Zamojski.
Post-doc in Waterloo University (Canada) and University of Maryland (USA) 1980/81 with Professor Bert Fraser-Reid.
Visiting Scientist in Duke University (USA) 1988/89 (host - Professor B. Fraser Reid).
Habilitation in 1990
Full Professor 1999

Head of the Ph.D. Studies at the Institute of Organic Chemistry, Polish Academy of Sciences (1998-2004)
Research Director of the Institute of Organic Chemistry (2004-2010)
Co-ordinator of the Center of Excellence in Development of New Therapeutics from Sugars (CEDNETS) (2003 – 2005)
Polish Representative in the ERA-Chemistry network (2006-2008)
Co-ordinator of the project: ‘Sugars as Raw Materials in the Synthesis of the Products with High-Added Value’ (ca. 6 mln euro) from European Regional Development Fund (POIG.01.01.02).
Director of the Institute of Organic Chemistry (2011-...)

Staff:

dr inż. Anna Korda; dr hab. inż. Zbigniew Pakulski; dr Anna Osuch-Kwiatkowska; dr Mykhaylo A. Potopnyk.

Ph.D. students:

mgr Bartosz Chaciak; mgr inż. Kinga Kuczyńska; mgr Katarzyna Łęczycka-Wilk; mgr Patrycja Sokołowska; mgr inż. Łukasz Szyszka; mgr inż. Karolina Tiara

Technicians:

Katarzyna Gwardiak; Romuald Karczewski.

Research activities

Three main topics are currently under investigation.

First one is connected with the modification of sucrose molecule at the terminal positions. 2,3,3',4,4’-Penta-O-benzyl- or 1’,2,3,3',4,4’-hexa-O-benzylsucrose (both synthesized for the first time in our laboratory) serve as starting materials for the preparation of many analogs. We are especially interested in the preparation of the crown ether analogs, also with other than oxygen heteroatoms in the macrocyclic ring, with incorporated sucrose unit and to study the complexation of chiral ammonium slats with such macrocycles. We proved that these compounds show high enantioselectivity towards alpha-phenylethylamine. We are also engaged in the preparation of sucrose receptors with higher (C2) symmetry and cryptands with sucrose scaffold.

Second topic is connected with the methodology of stereocontrolled preparation of carba- and aza-bicyclic sugar mimetics: derivatives of bicyclo[4.3.0]nonane and bicyclo[4.4.0]decane. These targets can be prepared via a multi-step synthesis from sugar allyltin derivatives. Recently we have proposed two alternative approaches towards such mimetics excluding (toxic) organostannanes.

Third topic is connected with the synthesis of biologically active oligosaccharides, triterpenes and saponins based on triterpenes isolated from white birch bark (lupane saponins), which have shown high cytotoxic activity

Selected scientific publications:

S. Jarosz Guest Editor: Current Organic Chemistry (2 issues): Simple sugars in organic synthesis: the stereochemical and biological aspects: part-I and part-II, 2014, 18, issue 13 and 14

Reviews and monographs

  1. Potopnyk, M.A.; Jarosz, S. Adv. Carbohydr. Chem. Biochem., 2014, 71, 227-295. Nitrogen-containing macrocycles having a carbohydrate scaffold
  2. Pakulski, Z.; Poly, F.; Dorabawila, N.; Guerry, P.; Monteiro, M. A. Curr. Org. Chem., 2014, 18, 1818–1845. 6-Deoxyheptoses in nature, chemistry, and medicine.
  3. Jarosz, S.; Nowogródzki, M.; Magdycz, M.; Potopnyk, M.A. RSC Special Periodic Reports Carbohydr. Chem., 2012, vol. 37, chapter 11 p. 303-325. Carbobicyclic sugar mimics.
  4. Queneau, Y.; Jarosz, S.; Lewandowski, B.; Fitremann, J. Adv. Carbohydr. Chem. Biochem. 2007, 61, 221-300. Sucrose Chemistry and Applications of Sucrochemicals.
  5. Jarosz, S.; Listkowski, A. Curr. Org. Chem. 2006, 10, 643-662. Sugar derived crown ethers and their analogs: synthesis and properties.

Original articles

  1. Tiara, K.; Potopnyk, M.A.; Jarosz, S. Beilstein J. Org. Chem. 2018, 14, 634. Synthesis of sucrose-based macrocycle with unsymmetrical monosaccharides "arms".
  2. Łęczycka-Wilk, K.; Dabrowa, K.; Cmoch, P.; Jarosz, S. Org. Lett., 2017, 19, 4596. Chloride-Templated Macrocyclization and Anion-Binding Properties of C2-Symmetric Macrocyclic Ureas Derived from Sucrose.
  3. Malik, M.; Jarosz, S. Org. Biomol. Chem., 2016, 14, 1764-1776. Synthesis of Polyhydroxylated Pyrrolidines from Bromonitriles through a Cascade Addition of Allylmagnesium Bromide/Cyclization/Reduction.
  4. Sidoryk, K.; Korda, A.; Rárová, L.; Oklešťková, J.; Pakulski, Z.; Strnad, M.; Cmoch, P.; Gwardiak, K.; Karczewski, R. Eur. J. Org. Chem. 2016, 373–383. Synthesis and cytotoxicity of 28a-homothiolupanes and 28a-homothiolupane saponins.
  5. Łęczycka, K.; Jarosz, S. Tetrahedron, 2015, 71, 9216-9222. Synthesis of novel macrocyclic derivatives with a sucrose scaffold by the RCM approach.
  6. Pakulski, Z.; Cmoch, P. Tetrahedron 2015, 71, 4757–4769. Study on the synthesis of regio- and stereoisomers of the disaccharide unit of the OSW-1 saponin.
  7. Malik, M.; Witkowski, G.; Jarosz, S. Org. Lett., 2014, 16, 3816-3819. Carboxybenzyl Group as an O-Nucleophile in the C-H Allylic Oxidation: Total Synthesis of (−)-Castanospermine.
  8. Potopnyk, M.A.; Jarosz, S. Eur. J. Org. Chem., 2013, 5117-5126. Synthesis and complexing properties of ‘unsymmetrical’ sucrose-based receptors.
  9. Malik, M.; Witkowski, G.; Ceborska, M.; Jarosz S., Org. Lett., 2013, 15, 6214-6217. Synthesis of polyhydroxylated quinolizidines and azaspiro[4.5]decanes from D-xylose.
  10. Potopnyk, M.A.; Cmoch, P.; Jarosz, S. Org. Lett., 2012, 14, 4258-4261. Short Synthesis of Diamide-Linked Sucrose Macrocycles.
  11. Potopnyk, M.A.; Lewandowski, B.; Jarosz, S. Tetrahedron: Asymmetry, 2012, 23, 1474-1479. Novel sucrose-based macrocyclic receptors for enantioselective recognition of chiral ammonium cations.
  12. Lewandowski, B.; Jarosz, S. Org. Lett., 2010, 12, 2532-2535. Amino-Acid Templated Assembly of Sucrose-Derived Macrocycles.
  13. Jarosz, S.; Lewandowski, B. Carbohydr. Res., 2008, 343, 965-969. Synthesis and complexing properties towards ammonium cation of aza-coronand analogues containing sucrose molecule.
  14. Lewandowski, B.; Jarosz, S. ChemComm, 2008, 6399-6401. Chiral recognition of alpha-phenylethylamine by sucrose-based macrocyclic receptors.
  15. Pakulski, Z. Synthesis, 2003, 2074-2078. Glycosylation in ionic liquids.
  16. Jarosz, S.; Mach, M. J. Chem. Soc., Perkin Trans. 1, 1998, 3943-3948. Phosphonate versus phosphorane method in the synthesis of higher carbon sugars. Preparation of D-erythro-L-manno-D-gluco-dodecitol.
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