An Efficient Lipase-Catalyzed Synthesis of Fatty AcidDerivatives of Vanillylamine with Antiherpetic Activity inAcyclovir-Resistant Strains

SANTIAGO N. CHANQUIA; ALICIA BALDESSARI; LAURA ALCHÉ; NADIA BOSCARO; GUADALUPE GARCÍA LIÑARES

Chemistry Select

Wiley VCH Verlag

Lugar: Weinheim; Año: 2017 vol. 2 p. 1537 - 1546

2365-6549

A series of eleven N-fatty acid derivatives of vanillylamine wassynthesized following an enzymatic approach, in excellent yieldand a chemoselective way. The excellent results obtained bycatalysis of Thermomyces lanuginosus lipase made the proce-dure very efficient, considering the low amount of enzymerequired and its lower price in co mparison with othercommercial lipases. The influence of various reaction parame-ters in the lipase-catalyzed reactions, such as enzyme source ,nucleophile/substrate ratio, enzyme/substrate ratio, solventand temperature, was studied. In order to evaluate the influence of the fatty acid chain length and configuration onthe reaction rate and yield, HPLC analysis and molecularmodeling experiments were performed. The results showedthat a chain length between 12?14 carbon atoms favors theactivity of the enzyme, while insaturation had no effect on thereaction rate. These facts confirm the experimental results. Inaddition, some of the evaluated compounds exhibited antiviralactivity against Herpes simplex virus type 1 (HSV-1) KOS strain(TK+) and Field and B2006 strains (TK-) in Vero cells.