Final Report Summary - HIPENZO (Enzymatic synthesis of organic molecules in alternative solvents)
Enzyme solubilisation in fluorous solvents and scCO2 by Hydrophobic Ion Pairing with perfluorinated surfactants was investigated. Various commercially available lipases capable of catalysing esterification and transesterification reactions were screened to select a lipase that could be efficiently ion paired with fluorinated surfactants. The complexation efficiencies of 60-70 % were achieved with several lipases giving 9-15 mg/ml [enzyme] in fluorous solvent. Two hydrophobically ion paired lipases Candida cylindracea and Pseudomonas cepacia demonstrated reasonable catalytic activity and good enantioselectivity towards the kinetic resolution of rac-1- phenylethanol in a perfluoromethylcyclohexane/hexane biphasic system. When HIP-lipases were employed for the ring-opening polymerisation of various lactones in fluorous biphasic system lipases Rhizopus arrhizus and Pseudomonas fluorescens were active and yielded polyesters. Further HIP-lipases were tested for the polycondensation polymerisation of polyesters. The ability to solubilise lipases in fluorinated solvents provided an opportunity to perform homogenous polymerisation of highly fluorinated monomers. Several hydroxyl-terminated fluorinated diols and fluorinated acids were examined in order to generate fluorinated polyesters with unique physical and chemical properties.