title: Inhibition of penicillin biosynthetic enzymes by halogen derivatives of phenylacetic acid.
abstract: The effect of phenylacetic acid (PAA) and several analogs on the activity of isopenicillin N synthase (IPNS) and acyl-CoA: 6-APA acyltransferase (AT) from Penicillium chrysogenum Wis 54-1255 has been tested. Whereas the substitution on the ring of a hydrogen atom by hydroxy-, methyl- or methoxy- groups did not cause any effect, the presence of halogens (Cl or Br) at positions 3 and/or 4 of PAA strongly inhibited these two enzymes. The replacement of hydrogen atoms by fluorine in certain positions also caused inhibition, but to a lesser extent.
authors.affiliation: Departamento de Bioquímica y Biología Molecular, Facultad de Veterinaria, Universidad de León, Spain.
authors.forename: H
authors.initials: H
authors.lastname: Martínez-Blanco
authors.forename: A
authors.initials: A
authors.lastname: Reglero
authors.forename: J M
authors.initials: JM
authors.lastname: Luengo
mesh_terms: D000217:Acyltransferases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D001966:Bromine; D002713:Chlorine; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D005461:Fluorine; D010088:Oxidoreductases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D046915:Penicillin-Binding Proteins; D010648:Phenylacetates / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D046915:Penicillin-Binding Proteins; D010648:Phenylacetates; D005461:Fluorine; D002713:Chlorine; D010088:Oxidoreductases; C038370:isopenicillin N synthetase; D000217:Acyltransferases; C018756:acyl-CoA-6-aminopenicillanic acid acyltransferase; D001966:Bromine