136656-96-7Relevant articles and documents
Towards a green enantiomeric esterification of R/S-ketoprofen: A theoretical and experimental investigation
Toledo, María Victoria,José, Carla,Collins, Sebastián E.,Ferreira, María Luján,Briand, Laura E.
, p. 52 - 61 (2015)
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 was studied at a molecular level through various spectroscopic techniques and molecular modeling. The results evidenced the dissolution of the polymeric support, loss of active protein, strong adsorption of the alcohols, modification of the secondary structure of the protein and smoothing of the inner structure of the biocatalyst's beads upon extended contact with the alcohols. Nevertheless, none of those drawbacks influences the specific activity and enantiomeric excess toward S(+)-enantiomer that remain unaltered upon extended contact with ethanol, 1- and 2-propanol as acyl acceptors. However, theoretical calculations demonstrated that methanol introduces steric and electronic hindrance within the step of the coordination of the R/S-ketoprofen with the catalytic triad.
Chemoenzymatic synthesis of pure enantiomeric 2-aryl propionic acids
Garcia,Del Campo,Llama,Sanchez-Montero,Sinisterra
, p. 8433 - 8440 (2007/10/02)
A new chemoenzymatic procedure to obtain pure enantiomeric 2-arylpropionic acids is described. The one pot synthesis of (±)-2-arylpropionic acids is carried out by addition of dichlorocarbene to the C=O bond of arylmethylketones and hydrogenolysis of the additon product. The racemic mixture is resolved by enantiospecific hydrolysis of the racemic ethyl esters using native lipase from Candida rugosa. The good yields, the accessibility of the starting arylmethylketones and the stereospecificity of the enzymatic hydrolysis make the process interesting in order to obtain the same non steroidal antiinflammatory drugs such as Ibuprofen or Naproxen.
