title: High performance liquid chromatography (HPLC) of natural products. IV. The use of HPLC in biosynthetic studies of cephalosporin C in the cell-free system.
abstract: A new cepham metabolite has been isolated from the filtered broth of Cephalosporium acremonium by high performance liquid chromatography (HPLC) and identified as 7 beta-(5-D-amino-adipamido)-3 beta-hydroxy-3 alpha-methyl-cepham-4 alpha-carboxylic acid (I). Pure penicillin N was prepared using HPLC in the analytical mode. When I was added in place of penicillin N as substrate for the cell-free biosynthetic of cephalosporin, no formation of deacetoxycephalosporin C (II) was observed. A synthetic cepham derivative, 7 beta-(5-D-aminoadipamido)-3-exomethylene-cepham-4 alpha-carboxylic acid (III) was also tested in the cell-free system as a possible intermediate. The compound III was shown to be an inhibitor of the ring expansion enzyme that converts penicillin N to deacetoxycephalosporin C.
mesh_terms: D000164:Acremonium / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D002474:Cell-Free System; D002511:Cephalosporins / Q000096:biosynthesis*; D002851:Chromatography, High Pressure Liquid; D010406:Penicillins / Q000302:isolation & purification
chemical_list: D000900:Anti-Bacterial Agents; D002511:Cephalosporins; D010406:Penicillins; C025163:cephalosporin C