The proposed project aims at the design of enzymatic conversions for the production of synthetically useful fluorinated chiral building blocks from epoxides. Halohydrin dehalogenases (HHDH), relatively new and still not sufficiently explored group of enzymes, will be used as biocatalysts. The strong focus will be on the evaluation of aqueous-organic solvent mixtures and pure organic solvents as reaction media. The use of organic media can offer significant advantages in the case of HHDH-catalysed transformations. In particular, it could lead to higher productivity, due to better solubility and stability of substrates. The target conversions are incorporation of cyano and azido groups through the HHDH-catalysed ring-opening reaction of fluorine-substituted aryl epoxides. The approach will be to select enzymes by screening a number of known wild-type and mutant enzymes. After the appropriate enzyme(s) and substrate(s) are selected, different organic solvents will be tested as media for the reaction, either as water-organic solvent mixtures or pure organic solvents. The important steric and electronic factors governing the catalytic activity, enantio- and / or regio-selectivity will be determined by using the molecular docking and QM/MM calculations in combination with the in silico mutagenesis study. The MD simulation in non-aqueous medium will be used for investigating the solvent effects on the structural and dynamic properties of HHDHs as well as their catalytic activity. Furthermore, enzyme(s) will be kinetically characterized in the selected reaction media and its operational stability will be evaluated. Kinetical model of the process will be developed in order to facilitate the reaction optimization. With the use of the kinetic model it is possible to determine the best reactor type for the investigated reaction, and to find initial conditions to achieve high productivity, substrate conversion and product yield without extensive experimental work.