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
Read the publication that featured this abstractA 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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