Search for content and authors

Application of 2-Nitroglycals in the Synthesis of Biologically Active Glycoconjugates

Katarzyna Komor 1Wiesław Szeja 1Grzegorz Grynkiewicz 2

1. Silesian University of Technology, Department of Organic Chem., Bioorganic Chem. and Biotechnol., Krzywoustego 4, Gliwice 44-100, Poland
2. Pharmaceutical Research Institute (IF), Rydygiera 8, Warszawa 01-793, Poland


It can be postulated that low molecular weight ligands, designed as drugs, can also be advantageously modified by chemical glycosylation using natural or synthetic sugars. Suitably selected sugar moieties can render pharmacophoric structures properties desirable in a pro-drug category. In particular, they can serve as: i) an active transport and biodistribution enhancers; ii) protection against phase II metabolism bioconjugation leading to excretion; iii) providers of a lipophilicity element needed for membrane, receptor and binding-pockets docking.[1]

Several classes of plant polyphenols are being studied (flavonols, catechins, isoflavones etc,) as antioxidants, detoxicants, chemoprotectants, immunomodulators, antitumor agents, regulators of lipids metabolism and cardiovascular health promoters.[2] The main reasons for slow progress in pharmaceutical development are their physicochemical properties, low bioavailability and unfavorable metabolism.

Glycals, which are readily available from sugars, can be an attractive starting material for glycoside bond formation. Their nucleophilic character at C-2 permits reactions with oxygen, nitrogen, and sulfur electrophiles that under high substrate stereocontrol generally lead to three-membered rings; ring opening under acid catalysis furnishes the corresponding glycosides [3]. Glycals also can be transformed into derivatives that have at C-2 an electron-withdrawing group and are amenable to Michael-type addition. A good example are 2-nitroglycals. In this case, glycoside bond formation is achieved under base catalysis and leads to 2-deoxy-2-nitroglycosides. These intermediates are readily converted into 2-amino-2-deoxyglycosides [4].

Focusing our attention on soya isoflavonoids, which are drug candidates in antitumor therapy research program, the chemical derivatization of genistein and biological activity study of its new derivatives has been started, aimed at anticancer compounds.

We report herein the regio- and stereoselective synthesis of O-glycosides, and glycoconjugates derivatives of aminosugars and genistein.

The effect of synthesized compounds on proliferation of cancer cells will be presented.


Research studies part-financed by the European Union within the European Regional Development Fund (POIG. 01.01.02-14-102/09).


[1] G.Grynkiewicz, W. Szeja, J. Boryski, Acta Poloniae Pharmaceutica – Drug Research, 2008, 64 (6)

[2] R.A. Dixon, Isoflavonoids: Biochemistry, Molecular Biology and Biological Functions, in Comprehensive Natural Product Chemistry ( D.H.R. Barton, Ed.,) Elsevier, vol.1 1999, 773

[3] W. Priebe, I. Fokt, G.Grynkiewicz, Glycal derivatives, synthesis and chemical reactions, in: “Glycoscience; Chemistry and Chemical Biology”2nd ed., (B. Fraser-Reid, K. Tatsuta, J. Thiem, eds.), Springer-Verlag, 2008.

[4] R. R. Schmidt, Y. D.Vankar, Accounts of Chemical Research, 2008, 41, 1059


Legal notice
  • Legal notice:

Related papers

Presentation: Poster at VII Multidyscyplinarna Konferencja Nauki o Leku, by Wiesław Szeja
See On-line Journal of VII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2010-03-15 12:27
Revised:   2010-04-06 21:38