Genistein is a naturally occurring polyphenol-type product with chemopreventive and antitumor potential. For example, genistein inhibits topoisomerase I and II , 5a-reductase  and protein histidine kinase, all of which may contribute to the antiproliferative or pro-apoptotic effects of genistein. Additionally, genistein has been shown to inhibit the growth of various cancer cells through the modulation of genes that are intimately related to the regulation of cell cycle and programmed cell death (apoptosis) [1]. Our previous experiments, among genistein modified at C7 by different unsaturated sugars, revealed that several compounds appeared more active than parent compound in preliminary screening for inhibition of cancer cell proliferation [2, 3]. The development of improved methods for carbohydrate synthesis and particularly glycosidic bond formation is crucial. Therefore, utilization of glycals as building blocks for the total synthesis of various natural products is of great interest in bioorganic and medicinal chemistry. We optimized an effective method for synthesis of new disaccharide building blocks from glycals, which are very useful chiral synthons in glycoconjugates synthesis.

Acknowledgment:

Research studies part-financed by the European Regional Development Fund (POIG.01.01.02-14-102/09); Katarzyna Komor recieved a scholarship under the project "DoktoRIS - Scholarship Program for Innovative Silesia".

References:

[1]   Banerjee, S.; Li, Y.; Wang, Z.; Sarkar, F.H. Cancer Letters, 2008, 269, 226-242
[2]  Rusin, A.; Zawisza-Puchałka, J.; Kujawska, K.; Gogler-Pigłowska, A.; Wietrzyk, J.; Świtalska, M.; Głowala-Kosińska, M.; Gruca, A.; Szej,a W.; Krawczyk, Z.; Grynkiewicz, G.;  Bioorganic and Medicinal Chemistry Lettetters, 2011, 19, 259-305
[3] Goj, K.; Rusin, A.; Szeja, W.; Kitel, R.; Komor, R.; Grynkiewicz, G.; Acta Poloniae Pharmaceutica – Drug Research, 2012, 69 (6), 1239-1247

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