Studies on antimicrobial activity of arginine-based surfactants and chemo- enzymatic synthesis of novel amphiphiles based on L-arginine and D-fagomine

Abstract

[EN] Amino acid lipid conjugates possess excellent surface properties, high biodegradability and low toxicity. Among them, arginine-based surfactants show a broad antimicrobial activity.

The mode of action of arginine-based surfactants was investigated. Thus, their interaction with membrane models (liposomes and phospholipid monolayers) and the effects caused on Staphylococcus aureus and Escherichia coli were studied

The antimicrobial efficacy of the arginine-based surfactants synthesised previously in our research group was improved. To this end, novel bis(phenylacetylarginine) derivatives were prepared chemoenzymatically.

Finally and with the aim of preparing novel antimicrobial agents, we prepared a new family of amphiphilic compounds, N-alkylated derivatives of D-fagomine, using fructose-6-phosphaste aldolase (FSA) as biocatalyst.

[ES] Los conjugados de lípidos y aminoácidos presentan excelentes propiedades tensioactivas, alta biodegradabilidad y baja toxicidad. De entre ellos, los derivados de arginina poseen un amplio espectro de actividad antimicrobiana.

Con el objetivo de elucidar el modo de acción de los tensioactivos derivados de arginina, se ha investigado su interacción con modelos de membrana (liposomas y monocapas de fosfolípidos) y se ha evaluado los efectos que causan en Staphylococcus aureus y Escherichia coli.

La eficacia antimicrobiana de los tensioactivos derivados de L-arginina previamente sintetizados en nuestro grupo de investigación se ha mejorado. Para ello, se ha preparado quimo-enzimáticamente una nueva familia de derivados de L-arginina, bis(fenilacetilargininas).

Finalmente y con el propósito de preparar nuevos posibles agentes antimicrobianos, se ha sintetizado una familia de compuestos anfifílicos, derivados alquilados de D-fagomina, empleando fructosa-6-fosfato aldolasa (FSA) como biocatalizador.