title: Direct enzymatic synthesis of natural penicillins using phenylacetyl-CoA: 6-APA phenylacetyl transferase of Penicillium chrysogenum: minimal and maximal side chain length requirements.
abstract: In vitro synthesis of different natural penicillins (hexanoyl, heptanoyl and octanoyl-penicillin) have been carried out by direct acylation of 6-aminopenicillanic acid (6-APA) with several fatty acid-CoA derivatives (hexanoyl-CoA, heptanoyl-CoA and octanoyl-CoA). The reactions were catalyzed by the enzyme Acyl-CoA: 6-aminopenicillanic acid acyltransferase from Penicillium chrysogenum AS-P-78. This enzyme only accepts as substrate, aliphatic side chain precursors whose carbon length is between 6 and 8 atoms. Although the enzymatic synthesis of octanoylpenicillin has been previously reported the in vitro synthesis of hexanoyl and heptanoyl penicillins is described here for the first time.
mesh_terms: D000217:Acyltransferases / Q000494:pharmacology*; D005227:Fatty Acids / Q000378:metabolism; D005285:Fermentation; D046915:Penicillin-Binding Proteins; D010406:Penicillins / Q000096:biosynthesis*; D010407:Penicillium / Q000201:enzymology*
chemical_list: D005227:Fatty Acids; D046915:Penicillin-Binding Proteins; D010406:Penicillins; D000217:Acyltransferases; C018756:acyl-CoA-6-aminopenicillanic acid acyltransferase