Isolation and application of β-galactosidases  in the synthesis of 2-deoxy-β-D-galactosides 

Przemysław Hahn 1Anna E. Kasprzycka 1Wiesław Szeja 1Mirosława Szczęsna-Antczak 2Tadeusz Antczak 2Mirosława Sioła 3Marian Zembala 3

1. Silesian University of Technology, Department of Organic Chem., Bioorganic Chem. and Biotechnol., Krzywoustego 4, Gliwice 44-100, Poland
2. Technical University of Łódź, Department of Biotechnology and Food Science, Stefanowskiego 4/10, Łódź 90-924, Poland
3. Silesian Center for Heart Diseases in Zabrze (SCCS), M. Curie-Sklodowskiej 9, Zabrze 41-800, Poland

Abstract

The biological significance of glycosides and glycoconjugates has stimulated many works on the development of methods for glycosidic bond formation.  They occur widely in natural products 2-deoxyglycosyl moieties are present in many biologically active compounds like anthracycline antitumour antibiotics, and aureolic acids, highly potent antimicrobial agents.  The anomerically selective enzymatic synthesis of 2-deoxy-β-D-glycosides is a very interesting approach in contrast to multi-stage chemical synthesis requiring the use of temporary groups equatorially disposed at C(2) which must be removed in later steps, often lowering reaction yields.

In this communication we report strategy to isolated β-galactosidase from different strains of yeasts and application in the synthesis of 2-deoxy-β-D-galactosides. Finally their fungitoxic activity were tested for yeasts (Candida albicans, Candida dubliniensis, Candida tropicalis, Candida glabrata, Candida krusei, Candida parapsilosis) isolated from clinical materials in the Laboratory of Microbiology, Silesian Center for Heart Diseases in Zabrze. tested for antifungal activity in cooperation with Silesian Centre of Heart Disease.

Acknowledgement

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

References:

[1] Demchenko AV, ed. 2008.Handbook of Chemical Glycosylation, Advances in Stereoselectivity and Therapeutic Relevance. Wiley-VCH. Weinheim

[2] Hou D.; Lowary T. L.; Carbohydrate Research; 344, (2009)l; 1911-19

[3] Petit J. M., Paquet F., Beau J. M., Tetrahedron Letters, 1991, 32, 6125–6128

[3] Trincone A., Pagnotta E., Rossi M., Mazzone M., Tetrahedron: Asymmetry, 2001, 12,  2783–2787

[4] Varki A, Cummings RD, Esko JD, Freeze HH, Stanley P, Bertozzi CR, Hart GW, Etzler ME. 2009. Essential of Glycobiology. Cold Spring Harbor Laboratory Press. New York

[5] Vic, G.; Hastings, J.; Crout, D.H.G. Tetrahedron Asymmetry7 (1996), 1973;

[6] Weymouth-Wilson AC. 1997. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 14:99-110

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Presentation: Poster at IX Multidyscyplinarna Konferencja Nauki o Leku, by Przemysław Hahn
See On-line Journal of IX Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2014-03-14 13:38
Revised:   2014-05-02 10:38
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