Plant latex peptidases as biocatalysts for the syntheses of amino acyl alkylamides

FAIT, M.E.; PADRÓ, J.M.; MÉNDEZ, L.; CLAPÉS, P.; MORCELLE, S.R.

Workshop; VII workshop on biocatalysis and biotransformations-1º simposio latinoamericano de biocatálisis y biotransformaciones; 2014

Results indicated that thermodynamic controlled synthesis was successful for the production of the Z-Ala alkylamides. Although relatively good yields were obtained for the synthesis under thermodynamic control of the Gly derivatives the formation of insoluble adducts in the case of the condensation reaction between Z-Gly-OH and Z-Leu-OH with the alkylamines avoided the full reaction, so the kinetic approach was tested. In this case, yields improved remarkably. For papain as biocatalyst, conversions of 99.1±0.3% in Z-Ala-NHC10 and 83.1±0.9% in Z-Ala-NHC12 after 72 h reaction. reaching conversions of 92.5±0.1% and 91.3±0.4% in Z-Gly-NHC10 and Z-Gly-NHC12, respectively, in 3 h reaction time. For the syntheses of the Z-Leu alkylamides by this approach, yields were 96±5% and 90±2% in Z-Leu-NHC10 and Z-Leu-NHC12 respectively after 72 h reaction. When araujiain was tested as biocatalyst, the best yields in Z-Ala-NHC10 and Z-Ala-NHC12 were 65.5±0.6% and 68±4% in 24 and 72 h respectively, whereas yields in Z-Gly-NHC10 and Z-Gly-NHC12 were 75±1% and 73±12% respectively (both after 72 h reaction). In the case of the synthesis of Z-Leu-NHC10 and Z-Leu-NHC12, the conversion yields were 22.31±0.06 (48 h) and 30±1% (72 h), respectively.