ASYMMETRIC HYDROGENATION OF C-C DOUBLE BOND OF N-PHENYL-2,3-DIMETHYLMALEIMIDES BY FUNGAL STRAINS

SOLA, BÁRBARA; ZACCHINO, SUSANA; SORTINO, MAXIMILIANO

Rosario

Congreso; XVI Congreso y XXXIV Reunión Anual Sociedad de Biología de Rosario; 2014

Most chiral syntheses are traditionally achieved through chemical methods employing an ever-expanding range of chiral catalysts and reagents. Chiral products obtained through bioconversions offer the advantage of employing a renewable and natural source of reagents and avoiding the use of solvents while operating at room temperature. Large numbers of microbes can be isolated from nature as a source of inocula for bioconversions. Filamentous fungi produces a myriad of useful enzymes with different catalytic abilities, providing the ability to mediate steps in organic syntheses. With the aim of increased the structural biodiversity of N-phenyl-2,3-dimethyl-maleimides through fungal catalysis, we isolated five fungal strains from soybean. Growing cells technique was used for biotransformation. Time of addition of the organic substrate profoundly affects the yield of product because the substrate may present toxicity toward cell growth. So, addition during the late logarithmic growth phase avoids toxicity effects. After 96 hours of the inoculation, all fungal strains arrive at this phase. Arthrinium phaeospermum, Aspergillus niger, Curvularia lunata, Fusarium solani and Rhizopus oryzae have demonstrated to be efficient biocatalysts for the enantioselective hydrogenation of 2,3-dimethylated-phenyl-maleimides, constituting new efficient tools for the production of chiral succinimides.