Towards A Green Kinetic Resolution Of R/S-Ketoprofen: A Theoretical And Experimental Investigation

M. V. TOLEDO; CARLA JOSÉ; SEBASTIÁN COLLINS; MARÍA LUJÁN FERREIRA; LAURA BRIAND

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2015 vol. 118 p. 52 - 61

1381-1177

Methanol, ethanol, 1- and 2-propanol were used as reactants and solvents in the esterification of R/S-ketoprofen catalyzed with Novozym®435. The interaction of the alcohols with Novozym®435 wasstudied at a molecular level through various spectroscopic techniques and molecular modeling. Theresults evidenced the dissolution of the polymeric support, loss of active protein, strong adsorption ofthe alcohols, modification of the secondary structure of the protein and smoothing of the inner struc-ture of the biocatalyst?s beads upon extended contact with the alcohols. Nevertheless, none of thosedrawbacks influences the specific activity and enantiomeric excess toward S(+)-enantiomer that remainunaltered upon extended contact with ethanol, 1- and 2-propanol as acyl acceptors. However, theoreticalcalculations demonstrated that methanol introduces steric and electronic hindrance within the step ofthe coordination of the R/S-ketoprofen with the catalytic triad.