Abstract
Abstract Lipase-catalyzed synthesis of eight fatty acid tyrosyl esters ( TyC 2 to TyC 18:1 ) was investigated using non commercial lipases from Rhizopus oryzae and Staphylococcus xylosus immobilized onto CaCO 3 . The monomolecular film technique was used to compare the ability of the various synthesized tyrosyl fatty acid esters to form a stable monolayer at the air/water interface and their capacity to interact with a phospholipid monolayer. The measurements of surface pressure versus the molecular area shows that, in contrast to tyrosol esterified with short and medium chains (acetic ( TyC 2 ), propionic ( TyC 3 ), caprylic ( TyC 8 ) and capric ( TyC 10 ) acids), tyrosol esterified with long chains: lauric ( TyC 12 ), palmitic ( TyC 16 ), stearic ( TyC 18 ) and oleic ( TyC 18:1 ) acids are able to form a stable monolayer at the air/water interface. A direct correlation was observed between the length of the saturated acyl chain of the derivatives and their corresponding collapse pressures. The presence of unsaturation reduces the collapse pressure value. The interaction of tyrosyl esters with a phospholipid monolayer was studied and the critical surface pressure ( π c ) of each ester was determined. Only medium and long chain ( TyC 8 to TyC 18:1 ) derivatives esters were found to interact efficiently with DiC 12 PC film.
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