Selection of biocatalysts for the synthesis of biodegradable surfactants with pharmaceutical, food and cosmetic applications

MORCELLE, S. R.; LIGGIERI, C.; OBREGÓN, D.; BRUNO, M.; PRIOLO, N.; CASTILLO, J.A.; MORÁN, M.C.; CLAPÉS, P.

Buenos Aires, Argentina

Congreso; Biolatina 2006: Impacto Socioeconómico de la Biotecnología. III Congreso Argentino de Biotecnología.; 2006

Foro Argentino de Biotecnología- UADE

ABSTRACT. Surfactants are one of the most representative chemical products with application in pharmaceutical, food and cosmetic industries, and consumed in large quantities on a worldwide scale. Since it is known that these compounds can adversely affect the aquatic environment, their biodegradability and biocompatibility have become almost as important as their functional performance to the consumer. Amino acid and peptide lipid conjugates constitute an interesting class of surfactants with good surface properties, antimicrobial activity and low potential toxicity. Due to the mildness and selectivity of enzymatic reactions, proteases can be used as catalysts for the formation of these compounds, avoiding the use of hazardous organic solvents and the formation of non desired chemical condensing by-products in the product final formulation. The aim of this work was to assay phytoproteases from native plant origin (belonging to the Asclepiadaceae and Bromeliaceae families) as biocatalysts for the preparation of arginine-based surfactants. Crude extracts with proteasic activity from Araujia hortorum, Asclepias curassavica, Funastrum clausum, Ananas comosus and Bromelia hieronymi were immobilized on polyamide and the condensation reactions were carried out in acetonitrile (0.25% water). Z-Arg-OMe and two alkylamines (decylamine and dodecylamine) were the substrates for the obtention of Z-Arg-decylamide and Z-Arg-dodecylamide respectively. Reactions were monitored by HPLC–MS. Papain was the reference biocatalyst for these condensation reactions. From this screening, araujiain (crude proteolytic extract from A. hortorum) gave the best results. This biocatalyst furnished up to 70% conversion by HPLC of the desired products, similar yields than those obtained with commercial papain.