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.

Biocatalyzed Synthesis of Vanillamides and Evaluation of Their Antimicrobial Activity / C. Pinna, P.A.M. Martino, G. Meroni, V.M. Sora, L. Tamborini, S.M.D. Dallavalle, M.L. Contente, A. Pinto. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 70:1(2022 Jan 12), pp. 223-228. [10.1021/acs.jafc.1c06213]

Biocatalyzed Synthesis of Vanillamides and Evaluation of Their Antimicrobial Activity

C. Pinna
Primo
;
P.A.M. Martino
Secondo
;
G. Meroni;V.M. Sora;L. Tamborini;S.M.D. Dallavalle;M.L. Contente
Penultimo
;
A. Pinto
Ultimo
2022

Abstract

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.
MsAcT; antimicrobial agents; biocatalyzed reactions; enzyme immobilization; flow chemistry; vanillamides;
Settore CHIM/10 - Chimica degli Alimenti
Settore CHIM/06 - Chimica Organica
12-gen-2022
29-dic-2021
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/894597
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