Redução de enonas empregando cultura de células em suspensão de Cereus peruvianus mill (cactaceae)

Abstract

Changes of biological exogenous substrates using plant cells in suspension allow achieve structural changes to provide useful substances. Thus, the biotransformation has become an important tool in the synthesis of organic compounds, mainly in obtaining chiral compounds of pharmaceutical interest. The purpose of this study was to define a methodology for biorreduction of enones, including a method for the extractive products. Were used as substrates for transbenzalacetophenone obtained synthetically, acetophenone and ethyl acetoacetate commercial, and racemics the standards used to monitor the reactions biocatalíticas have been synthesized and characterized by the NMR spectroscopic methods of 1H and 13C. It used two methodologies, that the first was to transfer 7.5 g of culture, Cereus peruvianus for MS medium, and that, after 5 days the cells were transferred to flask with 50,0 mL of solution 0,1 M phosphate-buffer (pH 7,0), and then added 30 mg of substrate(trans-benzalacetophenone and ethyl acetoacetate) Which were kept stirring for 5 days. After this period the supernatant was subjected to extraction with ethyl acetate. The second method consisted of transfer of 7,5 g of callus culture of Cereus peruvianus to flask with 50 mL of solution 0.1 M phosphate-buffer (pH 7.0), and then added 30 mg of substrate (trans-benzalacetophenone and acetophenone), which were kept in agitation for 5 days. After this period took place extraction of supernatant with butanol and ethyl acetate, the cells were sonicated and extraction with methanol. The product obtained was subjected to analysis by TLC and subsequent structural determination by the 1H and 13C NMR and GC-MS. Observed that the plant cells have the ability to reduce the double bond of transbenzalacetophenone, resulting in the 1,3-diphenyl-one-1, and not promoted carbonyl of reduction acetophenone of the ethyl acetoacetate. The yield of the reaction was 20%.