Microbial resolution of DL-N-benzyloxycarbonyl-p-hydroxyphenylglycine by Streptomyces zaomyceticus
Using DL-p-hydroxyphenylglycine umbelliferone carbamate as the probe, screening from soil was carried out for microbes capable of hydrolysing urethane-type derivatives. Out of 71 strains positive for umbelliferone liberation (fluorescent), 8 strains were able to hydrolyze DL-N-benzyloxycarbonyl-4-hydroxyphenylglycinc (I). One of such soil organism identified as Streptomyces zaomyceticus carried out this reaction in an enantio-selective manner. Optically active, pure D-N-benzyloxycarbonyl-4-hydroxyphenylglycine and L-4-hydroxyphenylglycine were obtained in crystalline form in 83 and 80% yields, respectively, after a 5-day incubation of the substrate (300 mg/100 mL) with this organism. In contrast to conventional L-acylase (EC 3.5.1.14) which can hydrolyze N-pbenylacetyl-4-hydroxyphenylglycine but not I, the enzymes responsible for the above resolution could cleave both substrates, indicating that they represent a unique type of amidohydrolase.