99499-12-4Relevant academic research and scientific papers
Biocatalyzed Synthesis of Vanillamides and Evaluation of Their Antimicrobial Activity
Contente, Martina L.,Dallavalle, Sabrina,Martino, Piera Anna,Meroni, Gabriele,Pinna, Cecilia,Pinto, Andrea,Sora, Valerio Massimo,Tamborini, Lucia
, p. 223 - 228 (2022/01/19)
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.
