HOMOCHIRAL ORGANOELEMENT ANALOGS OF NATURAL COMPOUNDS .1. BIOCATALYTIC METHODS FOR PRODUCTION OF FLUORINE-CONTAINING L-PHENYLGLYCINE AND D-PHENYLGLYCINE ON PREPARATIVE-SCALE

A convenient method was developed for production of homochiral o- and p-fluorophenylglycine by the enantioselective hydrolysis of their N-ac etyl or N-phenylacetyl derivatives with aminoacylase from Streptoverti cillium olivoreticuli or penicillin acylase from Escherichia coli to Y ield L-enantiomer. Acid deacylation of D-(N-phenylacetyl) derivatives is accompanied by partial (up to 15%) racemization. On the other hand, phenylacetyl derivatives of D-p- and D-o-fluorophenylglycine can be e fficiently hydrolysed without racemization with the use of penicillin acylase in high concentrations.