Biocatalyzed Synthesis of Vanillamides and Evaluation of Their Antimicrobial Activity

    • Cecilia Pinna1
    • Piera Anna Martino2
    • Gabriele Meroni2
    • Valerio Massimo Sora2
    • Lucia Tamborini3
    • Sabrina Dallavalle1
    • Martina L. Contente*1
    • Andrea Pinto1
    • 1Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, via Celoria 2, 20133 Milan, Italy
    • 2Department of Biomedical, Surgical and Dental Sciences (DSBCO), One Health Unit, University of Milan, via Pascal 36, 20133 Milan, Italy
    • 3Department of Pharmaceutical Sciences (DISFARM), University of Milan, via Mangiagalli 25, 20133 Milan, Italy

    A series of vanillamides were easily synthesized, exploiting an acyltransferase from Mycobacterium smegmatis (MsAcT). After their evaluation as antimicrobial agents against a panel of Gram-positive and Gram-negative bacteria, three compounds were demonstrated to be 9-fold more effective toward Pseudomonas aeruginosa than the vanillic acid precursor. Taking into consideration the scarce permeability of the Gram-negative bacteria cell envelope when compared to Gram-positive strains or yeasts, these molecules can be considered the basis for the generation of new nature-inspired antimicrobials. To increase the process productivity and avoid any problem related to the poor water solubility of the starting material, a tailored flow biocatalyzed strategy in pure toluene was set up. While a robust immobilization protocol exploiting glyoxyl-agarose was employed to increase the stability of MsAcT, in-line work-up procedures were added downstream the process to enhance the system automation and reduce the overall costs.

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