Biocatalyzed Synthesis of Vanillamides and Evaluation of Their Antimicrobial Activity.
Cecilia PinnaPiera Anna MartinoGabriele MeroniValerio Massimo SoraLucia TamboriniSabrina DallavalleMartina Letizia ContenteAndrea PintoPublished in: Journal of agricultural and food chemistry (2021)
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.
Keyphrases
- gram negative
- pseudomonas aeruginosa
- cystic fibrosis
- single cell
- mycobacterium tuberculosis
- randomized controlled trial
- escherichia coli
- staphylococcus aureus
- cell therapy
- climate change
- endothelial cells
- biofilm formation
- stem cells
- smoking cessation
- saccharomyces cerevisiae
- mesenchymal stem cells
- magnetic nanoparticles