Enzymatic synthesis of the penicillin and cephalosporin nuclei from an acyclic peptide containing carboxymethylcysteine.
The tripeptide delta-(L- carboxymethylcysteinyl )-L-cysteinyl-D-valine (L-CMC-CV) is converted sequentially into the CMC analog of isopenicillin N, the CMC analog of penicillin N, and the CMC analog of desacetoxycephalosporin C by, respectively, isopenicillin N synthetase, isopenicillin N epimerase, and desacetoxycephalosporin C synthetase, all isolated from the beta-lactam producing prokaryote Streptomyces clavuligerus.
D000591:Amino Acid Isomerases / Q000378:metabolism; D001426:Bacterial Proteins; D001681:Biological Assay; D002511:Cephalosporins / Q000096:biosynthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D004798:Enzymes / Q000378:metabolism; D009842:Oligopeptides / Q000378:metabolism; D010088:Oxidoreductases / Q000378:metabolism; D010406:Penicillins / Q000096:biosynthesis*; D013302:Streptomyces / Q000201:enzymology
D001426:Bacterial Proteins; D002511:Cephalosporins; D004798:Enzymes; D009842:Oligopeptides; D010406:Penicillins; C025578:deacetoxycephalosporin C; C041340:delta-carboxymethylcysteinyl-cysteinyl-valine; D010088:Oxidoreductases; C038370:isopenicillin N synthetase; C041342:desacetoxycephalosporin C synthetase; D000591:Amino Acid Isomerases; C040886:isopenicillin N epimerase; C006414:penicillin N