Polyesters Inspired by Glycerides: Enzymatic Polycondensation, Structure, Properties, and Nanoparticle Preparation

The polycondensation of glycerol and aliphatic dicarboxylicacidscatalyzed by Candida antarctica lipaseB absorbed on a macroporous acrylic resin (CALB) results in polyesterscomposed of repetitive units structurally similar to mono-, di-, andtriglycerides. Adipic, suberic, sebacic, and dodecanedioic acids wereinvestigated for the CALB-catalyzed polycondensation with glycerolin solution and bulk. In both conditions, the CALB-catalyzed esterificationof primary hydroxyl of glycerol and acyl migration occurs in paralleland results in branched polyesters. Higher molar mass polyesters wereobtained in reactions performed in bulk and using longer diacids thanin solution and using shorter diacids. These glyceride-like polyestershave different amphiphilicity and physical properties that changefrom more hydrophilic and amorphous for poly(glycerol adipate) tomore hydrophobic and semicrystalline for poly(glycerol dodecanedioate).The amphiphilicity of these polyesters allowed the production of nanoparticleswith a hydrodynamic radius in the range of 35-270 nm and anegative zeta potential.