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.
D000581:Amidohydrolases / Q000378:metabolism*; D002511:Cephalosporins / Q000032:analysis / Q000096:biosynthesis* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D005658:Fungi / Q000201:enzymology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
D002511:Cephalosporins; D000581:Amidohydrolases