Stereo-specific synthesis of 3-trifluoromethylcephalosporin derivative by microbial acylase

Cephalosporin acylase (EC 3.5.1.11) obtained from Kluyvera citrophila ATCC 21285 was found to catalyze synthesis of 7-[2-(2-thienyl)acetamido]-3-trifluoromethyl-3-cephem-4-carboxylic acid from methyl thienylacetate and dl-7-amino-3-trifluoromethyl-3-cephem-4-carboxylic acid. The enzymatically-synthesized compound showed [alpha]25 D + 42.7 degrees (c 0.058, MeOH) and its biological activity was about twice as much as that of racemic 7-[2-(2-thienyl)acetamidol]-3-trifluoromethyl-3-cephem-4-carboxylic acid chemicall synthesized. As a result, N-acylation by this enzyme was demonstrated to be asymmetric synthesis.